DE1470370A1 - Process for the production of new basic substituted pseudoindoles - Google Patents

Process for the production of new basic substituted pseudoindoles

Info

Publication number
DE1470370A1
DE1470370A1 DE19641470370 DE1470370A DE1470370A1 DE 1470370 A1 DE1470370 A1 DE 1470370A1 DE 19641470370 DE19641470370 DE 19641470370 DE 1470370 A DE1470370 A DE 1470370A DE 1470370 A1 DE1470370 A1 DE 1470370A1
Authority
DE
Germany
Prior art keywords
lower alkyl
old
given
group
pseudoindoles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
DE19641470370
Other languages
German (de)
Other versions
DE1470370B2 (en
DE1470370C3 (en
Inventor
Seeger Dr Ernst
Landgraf Dr Klaus
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of DE1470370A1 publication Critical patent/DE1470370A1/en
Publication of DE1470370B2 publication Critical patent/DE1470370B2/en
Application granted granted Critical
Publication of DE1470370C3 publication Critical patent/DE1470370C3/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

DR. F. ZUMSTEIN - DR. E. A88MANN - DR. R. KOENIOÖBERGERDR. F. ZUMSTEIN - DR. E. A88MANN - DR. R. KOENIOÖBERGER PATENTANWÄLTEPATENT LAWYERS

und aaienand aaien

TKLKQRAMMKi ZUMPAT POSTSOHKCKKONTOi MONOHKN 911 SBTKLKQRAMMKi ZUMPAT POSTSOHKCKKONTOi MONOHKN 911 SB

BANKKONTOt BANKHAUS H. AUPHKUSEI«BANK ACCOUNT BANKHAUS H. AUPHKUSEI «

8 MONOHEN a,8 MONOHS a,

BRÄUHAUeSTRAeSK Afm BRÄUHAUeSTRAeSK Afm

Caae 5/E72Caae 5 / E72

Br. larl fhoeae OebH., BtWraoh an 4er BitBr.larl fhoeae OebH., BtWraoh an 4er bit

▼erfahr«» sar B«rat«lliiBe von noaoa baalaoh aabatitaiortoa▼ experience «» sar B «rat« lliiBe from noaoa baalaoh aabatitaiortoa

PacadolnAolMnPacadolnAolMn

Bi· BrflBAnBf betrifft tin ferfaaren sur HeretelluBg aoaar aaalaoh attbetitulerUr Peeudolndol· der allceaeiaea VoraelBi · BrflBAnBf concerns tin ferfaaren sur HeretelluBg aoaar aaalaoh attbetitulerUr Peeudolndol · der allceaeiaea Vorael

sowie ihrer Salae alt physiologisch Tertragllohen anorganieohen oder organiBohen Sauren.as well as their salons old, physiologically sustainable, inorganic or organic acids.

16 316 3

BAD ORIGINALBATH ORIGINAL

U70370U70370

Xb der oolfen fonelXb the ololf fonel B| eise BrHqrlgntppe oder einen JaoBjlroe»,B | ice brHqrlgntppe or a JaoBjlroe »,

eis Vseeereteff«· oder eis BnlogonntoB, eine Biedereeis Vseeereteff «· or eis BnlogonntoB, a staid

Alkyl* oder f 1kff*»y"* ιAlkyl * or f 1 kff * »y " * ι

elBO Biedere Alkyl*r«pv« oder »Inen Fbem/lreet, der fegeeemnfnlle dnrok IhlogooBtOBe oder Biedere Alkyl- oder Alye eebetltnlert eeln Ip B4 einen nlederoB AUqrlreet,elBO Biedere Alkyl * r "pv" or "Inen Fbem / lreet, der fegeeemnfnlle dnrok IhlogooBtOBe or Biedere Alkyl- or Alye eebetltnlert eeln Ip B 4 a nlederoB AUqrlreet,

B^ eiaoB niederen AUrylreet oder einen λ B^B^B^K Bn^v ^Eb^b^bb^b^b^B Bn^niBnB^ft bb^b^Hb^b^b^bbb^b^K b^lv nn^B^HB ^ eiaoB lower AUrylreet or a λ B ^ B ^ B ^ K Bn ^ v ^ Eb ^ b ^ bb ^ b ^ b ^ B Bn ^ niBnB ^ ft bb ^ b ^ Hb ^ b ^ b ^ bbb ^ b ^ K b ^ lv nn ^ B ^ H

foeBttlgtoB BeteroejrelieelieBfoeBttlgtoB BeteroejrelieelieB

fBlie deroh eis welteree BeteremtoB «BteroroeiieB BBd/oder derail oIbob niederen Alftrlreet tabetltulert eelBfBlie deroh eis welteree BeteremtoB «BteroroeiieB BBd / or derail oIbob lower Alftrlreet tabetltulert eelB

BOdOBtet elBOB e^redkettieen oder rr*m%ig\an olvBlen BUBtetlBOBen rtfMOBQBOB·! otoffTet Bit S - 4 KoBleBetoff-BOdOBtet elBOB e ^ redkettieen or rr * m% ig \ an olvBlen BUBtetlBOBen rtfMOBQBOB ·! otoffTet Bit S - 4 KoBleBetoff-

werden die bobob ferMadua«OB daroB Oyellei·- elnee lBOB/UvdresoBe der VotboIthe bobob ferMadua «OB daroB Oyellei · - elnee lBOB / UvdresoBe der VotboI

II·II

9 O 9 B Π ι / ! s 3')9 O 9 B Π ι /! s 3 ')

BAD ORIGINALBATH ORIGINAL

• j -• j -

dor I1 bin R5 und A die obem angefahrten Bedeutungen auf« «•!•a«, is Gegenwart ti**· KoadmaatloBMlttel·, ««loh«·dor I 1 am R 5 and A the meanings approached above on «« •! • a «, is present ti ** · KoadmaatloBMlttel ·,« «loh« ·

bewirkt, erhalt«.cause, receive «.

Owalialerung erfolgt »·1 ftateratttre» ivlaohea 50 α. 180° C, TPgit Wi TtBMrAturflik «vl«ohen 80 oad 160° O, e*«*«j»afall· 1* G»e«WArt ei&MOwalialerung takes place »· 1 ftateratttre» ivlaohea 50 α. 180 ° C, TPgit Wi TtBMrAturflik «vl« ohen 80 oad 160 ° E, e * «*« j »afall · 1 * G» e «WArt ei & M

Al· IoBdtMatloinplttel, welch· Al« AMK>Blakab*palttttt£ bewlrkea, kMJiN Bortrifluurld o4«r M«re Katalye-v^y,.^, wie eokvefelalur*, HalageavMeeretoffeVvreB, PoIyphoe*vX)raIttre o4«r liAelilofid, <Α·τ So)mera*t«lllialoeenl4·, wie Kupfer-(I) -cblorid Vi eic·i-ohlorl«^U rKge. £1· jSeua$aaltt«lAl · IoBdtMatloinplttel what -Al "AMK> Blakab * palttttt £ bewlrkea, kMJiN Bortrifluurld o4" r M "re Katalye-v ^ y. ^ How eokvefelalur * HalageavMeeretoffeVvreB, PoIyphoe * v X) raIttre o4" r liAelilofid, <Α · τ So) mera * t «lllialoeenl4 ·, like copper- (I) -cblorid Vi eic · i-ohlorl« ^ U rKge. £ 1 · jSeua $ aaltt «l

okBÄßig polar· Iiuauttcanittel, «1· Alkohol·, bel-M Methanol, Äthanol oder *utanol, Glykole oder Blödere fettsäuren, wi« Keelgttore, elngesttet. Bei Verwandüb« ciekt polarer Loettngetdttel, wie Ohlorofom oder Benzolt 11·β·η die Aueeeutea niedriger.okBÄiges polar · liuauttcanittel, «1 · alcohol ·, bel-M methanol, ethanol or * utanol, glycols or stupid fatty acids, like Keelgtore, ingested. In the case of relatives, polar Loettngetdttel, such as Ohlorofom or benzene, t 11 · β · η the Aueeeutea lower.

Pie als *Mg»"€»»toffe verwendettn PhenylhydrMone derPie as * Mg »" € »» substances use phenylhydrons

XI werden naoh fibllohm Method·«, beleplelewele· geali -Weyl, Meth.d.Org.Ghali. f Bd. TXX, Teil I, 8. 461 ff hergMteilt. 8o erhilt mi, B, i-BiMthylMdso-V phea7l-peiitao<m-(4)-pbeti/lh7drejion auf folgende Welee:XI are naoh fibllohm Method · «, beleplelewele · geali-Weyl, Meth.d.Org.Ghali. f vol. TXX, part I, 8. 461 ff. 8o receives mi, B, i-BiMthylMdso-V phea7l-peiitao <m- (4) -pbeti / lh7drejion on the following Welee:

120,Og 1-4>i«ethrlam<lno-«V>plu»fli|rl->peBt«non-(4) werden la 200 ocm toluol gel5«t( mit 64,Og Phenylhytlreain vereetat120, Og 1-4> i «ethrlam < lno-« V> plu »fli | la r l-> PEBT "non- (4) 200 ocm toluene gel5" t (vereetat 64, Og Phenylhytlreain

909881 / 1633909881/1633

BAD ORIGINALBATH ORIGINAL

α*·** la liter 2-5 Staate* aett* BtUkflai fafcoea*, «ofcei la «Um« Wnaeerttoeofcelder Al· berechnete Meat· tr*wt wirt- laoh d« AMtetiillw« *#·α * · ** la liter 2-5 Staate * aett * BtUkflai fafcoea *, «ofcei la «To« Wnaeerttoeofcelder Al · calculated Meat · tr * wt wirt- laoh d «AMtetiillw« * # ·

«tr HUekeiaad Im Takutui fnOittoal«r«f I»o ^ 177 - 179° O,F- 60° C, Aeabmttti 89 + *«r th«orl·.«Tr HUekeiaad Im Takutui fnOittoal« r «f I» o ^ 177-179 ° E, F- 60 ° C, Aeabmttti 89 + * «r th« orl ·.

β1·1ο|ι·η ?«rfahr*B warden tm%«r um PheajUiydxmson· der Vox»·! XXβ1 · 1ο | ι · η? «rfahr * B warden tm%« r um PheajUiydxmson · the Vox »·! XX

di· fol«·»-di · fol «·» -

CBmCBm 4-Cn3 4-Cn 3 4-CB.O-C B4-CB.O-C B «4«4 >5> 5 AA. M RfM Rf F0CF 0 C 11 «J«J 4-<a4- <a Π> 6 5Π> 6 5 «5«5 OB,IF, -(οι,),-- (οι,), - 115115 22 «J«J BB. C8·C8 OH,OH, 64-6564-65 55 CB,CB, O6H5 O 6 H 5 CB,CB, on,on, -(CHj)2-- (CHj) 2 - -- 6868 44th «β«5«Β« 5 CH,CH, OB,IF, -CHj-gU-CHj-PDO 168-72/
0,05168-72 /
0.05

Bit fbrleen JPI^enjlhydrajtone wurden nicht gereinigt, sondern al· lohprodukte elngeettet. Die iu lJUrer HereteXlangBit fbrleen JPI ^ enjlhydrajtone were not cleaned, but all wage products are embedded. The iu lJUrer HereteXlang

Aalnoketone der PoraelEel noketones of the Porael

B1-C-B 1 -C-

XXXXXX

•lad «stwedwr litaraturlMfcaimt oder kanuwn aaeB tlbliohen Methoden, keiepitle««l8· &m*B t. filion, J.Ghm.Soo. 1«i5g. 8.6 - 9»• lad «stwedwr litärlMfcaimt or kanuwn aaeB tlbliohen methods, keiepitle« «l8 · & m * B t. filion, J. Ghm. Soo. 1 «i5g . 8.6 - 9 »

909881/1633909881/1633

BADBATH

ertalto» ν#*4·η· !»oh 41···γ NrttaoAo vurAo»ertalto »ν # * 4 · η ·!» oh 41 ··· γ NrttaoAo vurAo »

h«rgMt«lltih «rgMt« llti

■ι■ ι «e»5«E» 5 «4 I »5«4 I» 5 OB,IF, OB,IF, kk Kp0C^Hi HgKp 0 C ^ Hi Hg 11 "S"S. .(0B2)S-. (0B 2 ) S- cn,cn, -<0H,)2-- <0H,) 2 - 127-29/0,15127-29 / 0.15 ** OB,IF, -OH2OII2OOH2On2 -OH 2 OII 2 OOH 2 On 2 OR,OR, —(CHa)«—- (CHa) «- 1Ο2-0β/0,151Ο2-0β / 0.15 55 e«H5 e « H 5 OB,IF, OB,IF, —(OHa/n**- (OHa / n ** 108-11/0,3108-11 / 0.3 44th 01S 01 p 4-«,-0Λ 4 - «, - 0 Λ OB,IF, "•(QU·)«""• (QU ·)« " 126-91/0,1126-91 / 0.1 55 «j«J J-OB1(MJ6B4 J-OB 1 (MJ 6 B 4 (JH,(JH, -(OH,),--(OH,),- 113-14/0,3113-14 / 0.3 66th «5«5 4^X-O6H4 4 ^ XO 6 H 4 O6H5(CB2^O 6 H 5 (CB 2 ^ -(0Bj)2-- (0Bj) 2 - 114-15/0,11114-15 / 0.11 77th «J«J -<0H2)2-- <0H 2 ) 2 - 110-13/0,14110-13 / 0.14 ββ -(OU,)^- (OU,) ^ 168-70/0,2168-70 / 0.2

rerfahrantffaaftS extialtratn T«rbladunÄ·«. dtr fora·! I g«vUn«o)itttafelIa im ihr· Bllttr*»ddltionewüji· altrerfahrantffaaftS extialtratn T «rbladunÄ ·«. dtr fora! I. g «vUn« o) itttafelIa in her · Bllttr * »ddltionewüji · old

Bflur«D OberfUJu^ M«rd«a. Al· eoXoh·Bflur «D OberfUJu ^ M« rd «a. Al eoXoh

, SealgMlwr·, JBeosAlhar«, Salio/laAur«, Sltrontnetare und V»lB«iii»· Ib Betrmoht., SealgMlwr ·, JBeosAlhar «, Salio / laAur«, Sltrontnetare and V »lB« iii »· Ib Betrmoht.

909881/1633909881/1633

BADORlGtNALBADORlGtNAL

Dl· neaea Verbindungen basltim wertvolle therapeutisch· Bigeneeha/teB, lnabexiondere wirken al· anal£»tleoh.Dlneaea connections are basically valuable therapeutically Bigeneeha / teB, lnabexiondere act as anal £ »tleoh.

Pi· naeliatehenden Beispiele dienen rar näheren *rläot«rang der KrfiadungjExamples based on Piñaelia serve seldom a closer look the Krfiadungj

89,0 f roh·· Phenylhydraaon de· 1-Plp#ridlBO-5-iA«jyl· ρMtMWB (4) werden la 120,0 g ^ΐ····1β geltet und outer KQhlune ■!« 115,0 g Bortrifluorldätheret, T«rdUnnt alt der fleloben lecge Usceelg, Tereetst. Aneohlieeend wird der89.0 f raw · · Phenylhydraon de · 1-Plp # ridlBO-5-iA «jyl · ρMtMWB (4) are la 120.0 g ^ ΐ ···· 1β and outer KQhlune ■! «115.0 g of boron trifluoride ether, T« rdUnnt old der fleloben lecge Usceelg, Tereetst. The aneohlieeend

Ee«ktieo««n«at* »wel Stindea im Waeeerbe4 maf 90° G erbttat.Ee «ktieo« «n« at * »wel Stindea in Waeeerbe4 maf 90 ° G inherited.

destilliert «aan dl· flüchtigen Beetandteil· la Waaaar» straülTBJnun ao( aaobt den Bookataad alt 20 jtigtr Kalliaa» oarbonatlttamg alkali β oh t nlaart die organleohe Sobioht la Ittmr aufι trennt die ätherieohe L0aung ab and troekiMt •le alt Kalloaoarbonat. Mach de« Abdeetlllleren d«e Löeangaalttele freJctlenlert aan da· Rohprodukt la Takuua uad erhält 25,0 g 2-*etlvl-Vplieeyl->.(e-plperidliioÄthyl)-p*eudoin4oldistilled «aan dl · volatile component part · la Waaaar» straülTBJnun ao ( aaobt the Bookataad old 20 ydigtr Kalliaa »oarbonatlttamg alkali β oh t nlaart the organleohe Sobioht la Ittmr aufι separates the etherealohe L0llaung The Löeangaalttele releases aan the crude product la Takuua uad receives 25.0 g of 2- * etlvl-Vplieeyl ->. (e-plperidliioEthyl) -p * eudoin4ol

Bar Darrtelluag Am ^fdrochlorlde leet aaa die gereinigte laa· la «aeeerfrelea Ither uad fällt da· Sail Tomlentl^ duroh Begäbe τοη waaeerfreler, ätherieober SaIβaeure aaa.Bar Darrtelluag Am ^ fdrochlorlde leet aaa the cleaned laa · la «aeeerfrelea Ither uad falls da · Sail Tomlentl ^ duroh would give τοη waaeerfreler, ätherieober SaIβaeure aaa.

9 0 9 8 8 1/16 3 3 ßAD ORIGINAL9 0 9 8 8 1/16 3 3 ßAD ORIGINAL

Xur weiteren Reinigung kooht mb da· 8·!· ait Aceton mm end kristallisier* ·· au· Methanol/Äther um. F - 243 - 244° 0.For further purification, there is no more than 8% acetone mm end recrystallize * from methanol / ether. F-243-244 ° 0.

Aof dieselbe Vsl·· werten erhalten:
a) 2 Aof get the same Vsl values:
a) 2

το* Kp0 22 - 182 - 187° C (Hydrochloric I. - 240 - 244° 0) b) 2 Methyl«»3—ttienwl—3*( fl—Borpfaft^ JLwffÜtbTl) »neettdoipdol 9 m 200° Ο (Hydroohlorid f - 228° 0)το * Kp 0 22 - 182 - 187 ° C (Hydrochloric I. - 240 - 244 ° 0) b) 2 Methyl «» 3 — ttienwl — 3 * (fl — Borpfaft ^ JLwffÜtbTl) »neettdoipdol 9 m 200 ° Ο (Hydroohlorid f - 228 ° 0)

Beleniel 2:Beleniel 2:

6O9O g 1-BlBrthylaBlno-3-pheöyl«-i>«ntettoo-(4)-lAenylhjrdr*e<m w«rd«n ·Β··ΒΒ·η alt 30 oca abaolutea Äthanol b«l einer Bad» teaptratvr you 90 - 100° 0 feeohnolee». In diese 8oh»else trügt aaii 60,0 g we··erfreie· SinkQhlortd «In, wobei d;, feaperatar auf 100° 0 ansteigt« Dann erwttnet man fünf Standen Ib Ölbad auf 150° 0. Pie abgekühlte Raaktionraaevo wird aunlobat alt 100 oob Bensol und aneohlieBeod unter SlakOhlung Bit konaentrlerteB Aaajonlak bi· aur alkalleohen Beaktlon Ter-β et et. IHe BenBolaobloAt wird alt 100 oob Äther verdünnt und von der wfleerigen Sohioht abgetrennt, anschließend Behr-BaIa alt Vaaaar auageirmeohen und Bit KalluBoarbonat getrooknet· Saoh dea Abdaapfen des LOeungeaittel· wird der Kück-•tana Ib TaknuB deetilliert. Hon erhÄlt 32,0 g 2-aethyl-3-phenyl-V(M-4lBethjlaBlnoith7l)-peeadoindol tob Kp0 n 148 - 152° 0. 90988 1/163 36O 9 O g 1-BlBrthylaBlno-3-pheöyl «-i>« ntettoo- (4) -lAenylhjrdr * e <mw «rd« n · Β ·· ΒΒ · η old 30 oca abaolutea Ethanol b «l a bath» teaptratvr you 90 - 100 ° 0 feeohnolee ». In this 8oh "else aaii deceives 60.0 g soft SinkQhlortd" In, where d ;, feaperatar rises to 100 ° 0 "Then one warms five levels Ib oil bath at 150 ° 0. Pie cooled Raaktionraaevo becomes aunlobat old 100 oob Bensol and aneohlieBeod under SlakOhlung Bit konaentrlerteB Aaajonlak bi · aur alkalleohen Beaktlon Ter-β et et. IHe BenBolaobloAt is diluted 100 oob old ether and separated from the wfleerigen Sohioht, then Behr-BaIa old Vaaaar auageirmeohen and bit CalluBoarbonat getrooknet · Saoh dea draining of the LOeungeaittel · the Kück- • tana Ib TaknuB is de-distilled. Hon receives 32.0 g of 2-ethyl-3-phenyl-V (M-4lBethjlaBlnoith7l) -peeadoindole tob Kp 0 n 148 - 152 ° 0. 90988 1/163 3

BADBATH

U70370U70370

Salae «trrden berg··teilt·Salae «trrden berg ·· divides ·

Acetatacetate

HydroehlorldHydroehlorld HydrotiroaldHydrotiroald

91° c91 ° c

F * «44 - 245° OF * «44-245 ° E

T m 231° C. T m 231 ° C.

BeltBlel 3:BeltBlel 3:

100,0 β Phettjlhydraftozi dee 1-I>la»th]rleJrtiu}-3-pbeiqrll>entafiou~(4) viri« in der gleichen Neage tleeeelg «elBet, Λλμλ fB*t mb ein Oe«leoli roe 80O9O g konaentrlerter 8obwefelelhure uoA 470,0 f Sleeaelg hinan. Mas er* tret 5 ßt und en auf 100° G, eaigt la faaeeretrahlTakutte «of die Hilfte dee Tolua^na eis «al «tat eater KQbIaBg Kalluaoerbonat ble ear aUcalleohen Reaktion, hinaa. Sie frelgeaetste Bee β ithert aan aua nad freJctloulert flaok des Abdeatllliaren dee Löeungaalttele la Taknaai. ΆΙ· Aaaeatite betragt 29,0 g. Kp0^1 Ψ 148 - 152° 0.100.0 β Phettjlhydraftozi dee 1-I> la »th] rleJrtiu} -3-pbeiqrll> entafiou ~ (4) viri« in the same neage tleeeelg «elBet, Λλμλ fB * t mb an Oe« leoli roe 80O 9 O g Konaentrlerter 8obwefelelhure uoA 470.0 f Sleeaelg hinan. Mas er * step 5 ß and en to 100 ° G, eaigt la faaeeretrahlTakutte "of die Hilfte dee Tolua ^ na eis" al "tat eater KQbIaBg Kalluaoerbonat ble ear aUcalleohen reaction, hinaa. You frelgeaetste Bee β ithert aan aua nad freJctloulert flaok des Abdeatllliaren dee Löeungaalttele la Taknaai. ΆΙ · Aaaeatite is 29.0 g. Kp 0 ^ 1 Ψ 148 - 152 ° 0.

Xn glaiolier Veiae varde hergeetellttXn glaiolier Veiae varde made

▼o» KpOf11 · 152 - 153° C, ieaaan Hjdroohlorld bat 20ββ Ο aeavllst.▼ o »Kp Of11 · 152 - 153 ° C, ieaaan Hjdroohlorld bat 20β β Ο aeavllst.

909881/1633909881/1633

BAD ORIGINALBATH ORIGINAL

U70370U70370

gibt ma Wl 70° 0 portiooeweieegives ma Wl 70 ° 0 portiooeweiee

tu 100 ff tu 100 ff

imttr Mkrea 90 g 1~ pbeoylbydrasoa, wobei dl· fMpanrtar leicht ansteigt· An-•ohlleiewl ffttart MUi noA 2 8%aai«B bei 140° C nach, 11··* *er*«tet da· ltalctlon*e«BlB«h «lt Waaeer undimttr Mkrea 90 g 1 ~ pbeoylbydrasoa, where dl · fMpanrtar increases slightly · An • ohlleiewl ffttart MUi noA 2 8% aai «B at 140 ° C after, 11 ·· * * calculates that talctlon * e "BlB" holds waaer and

toimy tat 100° 0, Ua da· «Matauaeapjodokt lat. M· eaar· löeune alfcaUeiert mi «rter Hhlvae ■&«toi my tat 100 ° 0, Ua da · «Matauaeapjodokt lat. M · eaar · löeune alfcaUeiert mit« rter Hhlvae ■ & «

oaA eohUtttl* «1· abt*aohlad«n« But el* JLtter · VlVi9 wl· 1» 1«1·ρ1·λ a aaaf , waiter Wl ta«.oaA eohUtttl * «1 · abt * aohlad« n «But el * JLtter · VlVi 9 wl · 1» 1 «1 · ρ1 · λ a aaaf, waiter Wl ta«.

71.0 g71.0 g

I
wl· IkI.
wl · Ik

»9,0 f»9.0 f

Wt Wi « Ot*Wt Wi «Ot *

!■ Olba· 2! ■ Olba · 2

IMA iflfl.Q β Μ··IMA iflfl.Q β Μ ··

190 - IaO* 0 eHtitet.190 - IaO * 0 eHtitet.

1S9 -1S9 -

0,0,

909881/1633909881/1633

BAD ORIGINALBATH ORIGINAL

- ίο -- ίο -

Auf dl« gleiche fei·· «rfcältOn the same fei ·· «rfcält

•tterl )-9· eodolBdol• tterl ) -9 · eodolBdol

0909

1ΘΟ " 1ΘΟ "

217 - 219°β217-219 ° β

•u· *«■ sehen Ph*nyllijrdraeon de· i-DlJMthylMüno-3-• u · * «■ see Ph * nyllijrdraeon de · i-DlJMthylMüno-3-

- 165° 0, tyUroofalorlA F - 23« - 237°- 165 ° 0, tyUroofalorlA F - 23 "- 237 °

nicht f«r«lJBifft«n PhfcyUgrdrtson d·· >p«nt«BOB-<4)·not for «lJBifft« n PhfcyUgrdrtson d ·· > p «nt« BOB- <4) ·

• 15β - 14O0 O, tyfoMfclorU F - 207* O sieht firwimigfimm IhnqrUqrtnuM 4«· 1-:• 15β - 14O 0 O, tyfoMfclorU F - 207 * O sees firwimigfimm IhnqrUqrtnuM 4 «· 1-:

«ι %««oMlori« V · S44* 0«Ι%« «oMlori« V · S44 * 0

909881/1633 BAD ORiQfNAL909881/1633 BAD ORiQfNAL

• ti -• ti -

BeU»lol 6ιBeU »lol 6ι

Au· 40,0 g t-4>l«ethyl«elt»o-5-ph«iyl-p«ni»no»-(4)-(i>-tolylhyftrason) erhält aaa uf diteelfee Welee, wie la leUplel 5 beeefcrleben, 24,0 * 2,5-Pl»«tHyl-3-phtnyl-3-(e-<ii»ethylaai»oäthyl)-pe»ttdoindol tob Kp0 2 * *5β - 161° C, Aeueii ftrtloeee lfyiroohlorid naoh den uBkrletallleieren ακ·Au · 40.0 g t-4> l «ethyl« elt »o-5-ph« iyl-p «ni» no »- (4) - (i> -tolylhyftrason) gets aaa uf diteelfee Welee, like la leUplel 5 beeefcrleben, 24.0 * 2.5-Pl »« tHyl-3-phtnyl-3- (e- <ii »ethylaai» oäthyl) -pe »ttdoindol tob Kp 0 2 * * 5β - 161 ° C, Aeueii ftrtloeee lfyiroohlorid near the uBkrletalllee ακ ·

bei 220 - 222° C echaiUt.at 220 - 222 ° C echaiUt.

Xn fleiohtr Veite «erdea «tie den eatepreelieiideA Theqyl erhalten:Xn fleiohtr Veite «erdea« tie the eatepreelieiideA Theqyl obtain:

e)e)

Ip0 13 - 158 - 159° C, Hjörochlorid J « 226° CIp 0 13-158-159 ° C, hydrochloride J «226 ° C

b) 2-iietturl«»3-i>heiurI-( t-dlaethylaJilneltterl) -5->a·thorr- b) 2-iietturl «» 3-i> heiurI- (t-dlaethylaJilneltterl) -5-> a · thorr-

το» Kp0 1 ■ 165 - 1T5° 0, Hydroohlorid F · 212 - 14° Cτο »Kp 0 1 ■ 165 - 1T5 ° 0, hydrochloride F · 212 - 14 ° C

o)O)

-T-mithoxr--T-mithoxr-

tob Ip0 15 - 170 - 182° C, Jtydrochlorid 7 « 237 - 239*tob Ip 0 15 - 170 - 182 ° C, hydrochloride 7 «237 - 239 *

d)d)

tob Ip0 n « 180 - 185° O1 Hydrochloric P * 225° Ctob Ip 0 n «180 - 185 ° O 1 Hydrochloric P * 225 ° C

' >i: 909881/1633'> i: 909881/1633

BADBATH

.· 12 -. · 12 -

7t7t

Aus 95tO g nioht gereinigt·» Phenylhydraeon dee 1-DieethylaaiBO-4 >~plienyl-hexejDon-(5) gewinnt nan nach der la Beispiel «aeegebeneo Methode 41,0 g 2~lfethyl-3-pbenyl-3-(/t-di»etl:yl aelaopropyD-peeudoindol tob Kp0 q^ ■ 165 - 169° C. Rydroofelorid F * 214 - 215° C (Methenol/ither).Not purified from 95 tons · »Phenylhydraeon dee 1-Dieethyl-3-pbenyl-3 - (/ t-di »etl: yl aelaopropyD-peeudoindol tob Kp 0 q ^ ■ 165 - 169 ° C. Hydroofelorid F * 214 - 215 ° C (methenol / ither).

6;6;

peeudolndol and 2~lie-thyl--3-Phanyl-5"(BHllae-thylejilno«B>fWthyl'-peeudolndol and 2 ~ lie-thyl - 3-phanyl-5 "(BHllae-thylejilno« B> fWthyl'-

a) Au· 50,0 g «Ines Gesteohea der Hienylhjrdrcuione Ton 2-DieethylejBino-4-pheDyl~hexancD~( 5) und von 1-Dlaethylattino· 2-»etliyl-3-ph«nyl-pentaiion"(4) lseeen eich la dereelben felee, wie la Beiepiel Z beeohrieben, 12,0 g elnee Cemieehee der beiden oben genannten Verblödungen von Sp0 ~~ * 148 - 155° C gewinnen. Zur Trennung Ik die beiden Komponenten nln&t »an das Dee ti Hat Ib Petrolfittaer auf und •rh&lt beim Abkühlen 6 g defl eines Ieoneren, T · 98 - 99° C1 de«een Hydroohlortd b*i ??4° C eoh»ilet (au· Sesigeeter/ Methanol).a) Au · 50.0 g «Ines Gesteohea of the hienylhjrdrcuione clay 2-DieethylejBino-4-pheDyl ~ hexancD ~ (5) and of 1-Dlaethylattino · 2-» etliyl-3-phenyl-pentaiion "(4) lseeen eich la dereelben felee, as la example Z beeohrieben, 12.0 g elnee Cemieehee of the two above-mentioned stupidities from Sp 0 ~~ * 148 - 155 ° C. To separate Ik the two components nln & t »to the Dee ti Hat Ib Petrolfittaer on cooling, it rises 6 g of an ion, T · 98-99 ° C 1 de «een Hydroohlortd at ~ 4 ° C eoh» ilet (external eter / methanol).

b) Dl« PetrolÄtheneutterlauge von a) befreit nan tob Löeung«- mlttel tmd fraktioniert den Ruckstand In Vakut». Sie Fraktionb) Dl "petroleum ether liquor from a) frees nan tob solution" - mlttel tmd fractionates the residue in vacuo ». You faction

909881/1633909881/1633

BAD ORIGJNALBAD ORIGJNAL

U70370U70370

voa Kp0 n ■ 152 - 158° C trenn« ma ab und isoliert dar oh weiter·· Kristallisieren aus Petroläther in der Kaute das reetliohe leoaere rom F ■ 9β - 99° C. I>ie Mutterlauge Ton der leisten Kristallisation dasrjft »an ein und löet das sarttokblelbende Ol in Äther. Hit Ittherlsoher Salselure wird da« Hydroohlorld des «weiten Ieoaeren ausgefällt, das bei 190° C schallst. Bs konnte nooh Blent f*kltrt «erden, welche der beiden oben angefahrten Fonein den Isoaerwn a) und b) *otsprechen.voa Kp 0 n ■ 152 - 158 ° C separate and isolate it oh further ·· Crystallization from petroleum ether in the chew the reetliohe leoaere rom F 9β - 99 ° C. The mother liquor clay that leads to crystallization and dissolve the sarttokblelbende oil in ether. Hit Ittherlsoher Salselure there is precipitated the "Hydroohlorld of the" wide Ieoaeren, which resounds at 190 ° C. No one was able to find out which of the two Fonein the isoaerwn a) and b) * ot speak.

Aus 100,0 g rohes Phenylfcydr&son des i-Dia-thylasdno-3,4-diphe»yl-butaB«a-(4) erhalt man bei gleleher Arbelt weise wie Sb Beispiel 2 beeohrteben 29,0 « 2,3-Diphenyl-3-(I-ditthjrl-aeinotthyD-pseudoindoi tob Xp01 - 185 - 190° C. F · 87° C mm rVkroltther. Hydroohlorid F - 178° C.From 100.0 g of crude Phenylfcydr & son of i-Dia-thylasdno-3,4-diphe "yl-butaB" a- (4) one obtains 29.0 «2,3-diphenyl- (4) in the same way as Sb Example 2 3- (I-ditthjrl-aeinotthyD-pseudoindoi tob Xp 01 - 185 - 190 ° C. F · 87 ° C mm rVkroltther. Hydroohlorid F - 178 ° C.

IB de*IB de *

weis· erhilt warnt weis · received warns

β (Hrdjpoohlerid F · 2OC - 206° C) FlienjlhTdraaon de« 1-Dieethyl-β (Hrdjpoohlerid F 2OC - 206 ° C) FlienjlhTdraaon de «1-Dieethyl-

909881/1633909881/1633

BADBATH

Beispiel IQtExample IQt

2-ieetkrl-3-iihenyl-3-/¥-( B-pfaenyllthyl-wthyl-amino )-Mtftyl7-peeodoindol2-ieetkrl-3-iihenyl-3- / ¥ - (B-pfaenylthyl-ethyl-amino) -Mtftyl7-peeodoindole

▲as de* nicht gereinigten Pltenylhydrason des 1-(ß-Phenjl-KtliylHMthylaiilDo)-3-phenylpentanon~(4) gewinnt neu auf dieselbe f·!··, wi· ie Beispiel 1 beschrieben, 2-Methyl-3-ß-phenyl B thy l-»e thyl-ejiino) -äthyj^-pe «ud oindol▲ as de * unpurified pltenylhydrasone of 1- (ß-Phenjl-KtliylHMthylaiilDo) -3-phenylpentanone ~ (4) gains 2-methyl-3-ß-phenyl to the same f ·! ··, as described in Example 1 B thy l- "e thyl-ejiino) -äthyj ^ -pe" ud oindole

το« Kp0 15 * 200 - 210° C, Oxalat F « 170° C.το «Kp 0 15 * 200 - 210 ° C, oxalate F« 170 ° C.

11»11 »

22,0 g nicht gereinigtee Phtnylhydraaon de· i-5HMthyl-peirt«2ion-(4) werden in 25 oo« abeolatea Athmnol ■lt 40,0 g «a«Mrfreie« ZinkohloriA 5 Stunden mm Küokflui «rhltrk and «it ia Beispiel 2 aofgearbeitet. Vi «erden 14,0 g 2,3-Dimrkhyl-3-(i^iBetliyleÄlno-tth3rl)-peett«oin4ol το· Cp0 Q7 ■ 79 - 80° C gewonnen. Uydroohlorld F * 209° C (■etfcanolAtlier).22.0 g not gereinigtee Phtnylhydraaon de · I 5HMthyl-peirt "2ion- be (4) in 25 oo" abeolatea Athmnol ■ lt 40.0 g "a" Mrfreie "ZinkohloriA 5 hours mm Küokflui" rhltrk and "it ia Example 2 aof worked. 14.0 g of 2,3-dimethyl-3- (i ^ iBetliyleAlno-tth3rl) -peett «oin4ol το · Cp 0 Q 7 · 79-80 ° C. are obtained. Uydroohlorld F * 209 ° C (■ etfcanolAtlier).

909881/1633909881/1633

ßA ORIGINALßA ORIGINAL

Claims (2)

In derIn the E1 eine Jfethy!gruppe oder einen Phenylreet,E 1 a Jfethy! Group or a Phenylreet, Ug ein Wfteeeretoff- oder ein Halogenatoa, eine niedere Alkyl» oder Alkoxygruppe, Ug is a Wfteeeretoff- or a Halogenatoa, a lower alkyl or alkoxy group, R, «ine niedere Alkylganipp® oder «ixum PTasn^liMi'% , ila** gegebenen falle duroh Ualogenatooe oder niaaüi-® AlJ^l- oder Alkoxygruppen eabetituiert ββin kann,R, «ine lower Alkylganipp® or« ixum PTasn ^ liMi '%, ila ** given fall duroh Ualogenatooe or niaaüi-® AlJ ^ l- or alkoxy groups substituted ββin, B^ einen niederen Alkylreet,B ^ a lower alkyl reet, Be einen niederen Alkylreet oder einen Aralkylreet, bedeuten, wobei K. und Rc euoh eueaeaten alt dea Btioketoffatoei einen geeHttigten heterocyclischen Ring, der gegebenenfalle durch ein weiteres Heteroatom unterbrochen und/oder durch einen niederen Alkylreet eubetltulert sein kann, bedeuten können, andBe is a lower alkyl or an aralkyl, where K. and Rc euoh eueaeaten old dea Btioketoffatoei a saturated heterocyclic ring, if applicable interrupted by a further hetero atom and / or can be replaced by a lower alkyl group, can mean, and 9 09 8 Ö 1 /16339 09 8 Ö 1/1633 ÖAD ORIGINALÖAD ORIGINAL A «inen bivalenten aliphatischen Kohlenwasserstoffrest alt 2 - 4 Kohlenstoffatomen bedeutet,A «inen divalent aliphatic hydrocarbon radical old 2 - 4 carbon atoms means ο ο wie von ihren SäureatttUticnesalstm, dadurch geke&nst lohnet, rtaß man ein Phenylhydrason dir Yortnsx ο ο as from their acidic acidity, thereby gaining reward , a phenylhydrasone was given to you Yortnsx in Aer B1 bie Hc und A dl<» angegebenen Bedeutungen eujtweieen, in Oegenwart eine*? K.ond«seetionemittolef welcJiee AeooniaJcabepaliing bewirkt, oycllsiert unn rtitj erhaltene Verbindung gewünoahtenfalls nach üblichen ISethoAon Im ein wöureadditione-•ale alt einer phyeielogieofc vertrfigliohen anorganischen oder organischen Stur« überfuhrt.in Aer B 1 bie Hc and A dl <»eujtweieen the meanings given, in Oegenwart a *? K.ond "seetionemittole f what aeooniaJcabepaliing brings about, oycllized unnaturally obtained compound if desired according to the usual ethoAon in a word addition - all old a phyeielogieofc compatible inorganic or organic struc" transferred. 2. Verjähren nach Anspruch 1, dadurch gekanneelohnet. da6 ale Kondenaalionsmittel Bortritluorid, Schwefelsäure, Chlorwasserstoff, PolyphosphoxeMvre, TünkchXorid oder ein al !halogenid -verwendet wird.2. Statute of limitations according to claim 1, thereby gekanneelohnet. DA6 ale Kondenaalionsmittel Bortri t tetrafluoride, sulfuric acid, hydrogen chloride, PolyphosphoxeMvre, TünkchXorid or is al halide -Uses!. BAD ORlGINAL 909881/1633 BAD ORlGINAL 909881/1633
DE1470370A 1964-06-05 1964-06-05 Basically substituted pseudoindoles and a process for their preparation Expired DE1470370C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
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DE1470370A1 true DE1470370A1 (en) 1970-01-02
DE1470370B2 DE1470370B2 (en) 1974-02-28
DE1470370C3 DE1470370C3 (en) 1974-10-10

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DE (1) DE1470370C3 (en)
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GB (1) GB1093912A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006128A1 (en) * 1978-06-08 1980-01-09 Dr. Karl Thomae GmbH 2,3-Dihydro-2-methyl-3-(2-(dimethylamino)-propyl)-3-phenyl-1H-indol-1-carboxaldehyde, process for its preparation and pharmaceutical preparations containing it

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006128A1 (en) * 1978-06-08 1980-01-09 Dr. Karl Thomae GmbH 2,3-Dihydro-2-methyl-3-(2-(dimethylamino)-propyl)-3-phenyl-1H-indol-1-carboxaldehyde, process for its preparation and pharmaceutical preparations containing it

Also Published As

Publication number Publication date
GB1093912A (en) 1967-12-06
CH457433A (en) 1968-06-15
DE1470370B2 (en) 1974-02-28
FR4423M (en) 1966-09-12
DE1470370C3 (en) 1974-10-10

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