FI59243C - PROCEDURE FOR FRAMSTATION OF N- (1-EECL-ALPHA-PYRROLIDYLMETHYL) -2-METOXY-5-SULPHAMIDOBENZAMIDE - Google Patents
PROCEDURE FOR FRAMSTATION OF N- (1-EECL-ALPHA-PYRROLIDYLMETHYL) -2-METOXY-5-SULPHAMIDOBENZAMIDE Download PDFInfo
- Publication number
- FI59243C FI59243C FI2549/72A FI254972A FI59243C FI 59243 C FI59243 C FI 59243C FI 2549/72 A FI2549/72 A FI 2549/72A FI 254972 A FI254972 A FI 254972A FI 59243 C FI59243 C FI 59243C
- Authority
- FI
- Finland
- Prior art keywords
- pyrrolidylmethyl
- ethyl
- methoxy
- sulfamido
- pyridine
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Description
m rt1>KUULUTUsjuLKAisu egon jBft m ^UTLÄGGNINGSSKAIFT5^40 :';i li o n e. Lii ayon.; tiy -0 07 i , 31 V5v3 Patent meddelat ^ T ^ (51) Kv.ik?/int.a.3 C 07 D 207/09 SUOMI—FINLAND (M) 25U9/72 (22) Haktmitpaivi —Anaekningadtg 15·09·72 (23) Alkupa*·—GlMghMadac 15-09·72 (41) Tulkit lulklMkal — Mvlt offuMlIg lU.12.73m rt1> ADVERTISEMENT egon jBft m ^ UTLÄGGNINGSSKAIFT5 ^ 40: '; i li o n e. Lii ayon .; tiy -0 07 i, 31 V5v3 Patent meddelat ^ T ^ (51) Kv.ik? /int.a.3 C 07 D 207/09 FINLAND — FINLAND (M) 25U9 / 72 (22) Haktmitpaivi —Anaekningadtg 15 · 09 · 72 (23) Alkupa * · —GlMghMadac 15-09 · 72 (41) Tulkit lulklMkal - Mvlt offuMlIg lU.12.73
Patentti- ja r.kirt.rthallltu. n»*»^ μ kuuLJunuu™ pvm. -Patent and r.kirt.rthallltu. n »*» ^ μ monthJun ™ date. -
Patent· och ragiatarstyralsan 7 Amskm uttagd odi «UkrifMn pubUcw-ad 31.03· oi (32)(33)(31) Pyydetty MuoUum—fagird prtorttut 13.06.72Patent · och ragiatarstyralsan 7 Amskm uttagd odi «UkrifMn pubUcw-ad 31.03 · oi (32) (33) (31) Pyydetty MuoUum — fagird prtorttut 13.06.72
Sveitsi-Schweiz(CH) 8813/72 Toteennäytetty-Styrkt (71) Fratmann SA, 5, Chemin du Mont-Blanc, Ch£ne-Bougeries, Geneve,Switzerland-Schweiz (CH) 8813/72 Proven-Styrkt (71) Fratmann SA, 5, Chemin du Mont-Blanc, Ch £ ne-Bougeries, Geneva,
Sveit s i-Schveiz(CH) (72) Eric Denzler, Zurich, Sveitsi-Schweiz(CH) (7M Berggren Oy Ab (5C) N-(l-etyyli-°^-pyrrolidyylimetyyli)-2-metoksi-5-sulfamidobentsainidin valmistusmenetelmä - Förfarande för framställning av N-(1-etyl-as-pyrroli dylmetyl)-2-metoxi-5~sulfamidobent sami dSwiss Switzerland (CH) (72) Eric Denzler, Zurich, Swiss Switzerland (CH) (7M Berggren Oy Ab (5C) N- (1-ethyl-β-pyrrolidylmethyl) -2-methoxy-5-sulfamidobenzidine Manufacturing method - Preparation of N- (1-ethyl-as-pyrrole dimethyl) -2-methoxy-5-sulfamidobenz Sami d
Keksintö koskee yksinkertaista ja edullista menetelmää, jonka avulla voidaan valmistaa N-(l-etyyli-a-pyrrolidyylimetyyli)-2-metok-si-5-sulfamidobentsamidia, jota voidaan käyttää mahan- ja suolenseu-dun sairauksien hoidossa samoin kuin lääkkeenä psykiatrian alalla.The invention relates to a simple and advantageous process for the preparation of N- (1-ethyl-α-pyrrolidylmethyl) -2-methoxy-5-sulfamidobenzamide, which can be used in the treatment of gastrointestinal diseases as well as in the field of psychiatry.
Tämä keksinnön mukainen valmistustapa on tunnettu siitä, että annetaan N-etyyli-a-aminometyyli-pyrrolidiinin reagoida fosfori-oksikloridin kanssa, jolloin tulokseksi saadaan N,N' ,N"-(l-etyyli-a-pyrrolidyylimetyyli)-fosforiamidia ja tämän annetaan välittömästi reagoida 2-metoksi-5~sulfamidobentsoehapon kanssa.This preparation according to the invention is characterized in that N-ethyl-α-aminomethyl-pyrrolidine is reacted with phosphorus oxychloride to give N, N ', N "- (1-ethyl-α-pyrrolidylmethyl) -phosphoramide and this is allowed react immediately with 2-methoxy-5-sulfamidobenzoic acid.
Liuottimena ja reaktion väliaineena käytetään tällöin pyri- diiniä.Pyridine is then used as the solvent and the reaction medium.
Käyttämällä keksinnön mukaisesti pyridiiniä liuottimena ja reaktion väliaineena saadaan se etu, että pyridiini toimii samanaikaisesti liuottimena ja happoa sitovana aineena ja tarjoaa siten sen käytännössä erittäin tärkeän edun, että aminiemäksen ja fosfori-oksikloridin väliset reaktiot voidaan toteuttaa peräkkäin yhtenä ainoana työvaiheena yhdessä ja samassa astiassa tarvitsematta välillä erottaa mitään väli- tai sivutuotteita.The use of pyridine as solvent and reaction medium according to the invention has the advantage that pyridine acts simultaneously as solvent and acid scavenger and thus offers the very important advantage that the reactions between amine base and phosphorus oxychloride can be carried out sequentially in a single operation in one and the same vessel without distinguish any intermediate or by-products.
Keksinnön mukainen valmistusmenetelmä tapahtuu seuraavan reak-tiokaavan mukaan: 2 59243 POCr, + 3 H0N-CHo—L J ., . . . ; 3 2 2 \N/ pyndxim °2H5 N-etyyli-a-amino- metyyli-pyrrolidiiniThe preparation process according to the invention takes place according to the following reaction formula: 2 59243 POCr, + 3 H0N-CHo-L J.,. . . ; 3 2 2 \ N / pyndxim ° 2H5 N-ethyl-α-aminomethyl-pyrrolidine
COOHCOOH
PO HN-CHp —l J + 3 HC1 + 3 JL JPO HN-CHp —l J + 3 HCl + 3 JL J
h2nso2 ^h2nso2 ^
CpH c L 2 5 3 N,Nf ,Ν"-(l-etyyli-α- 2-metoksi-5-sulfamido- pyrrolidyylimetyyli)^fosforiamidi bentsoehappo -» pyridiini CO-NH-CHp—k. ) 3 /^V°CH3 ^ I c2h5 * po,,h3 H NS02/X/ fosforihappo N-(1-etyyli-a-pyrrolidyyli-metyyli)-2-metoksi-5-sulf-amidobentsamidi . Keksinnön mukainen menetelmä voidaan toteuttaa käytännössä yksinkertaisella tavalla siten, kuin on esitetty seuraavassa suoritus-esimerkissä:CpH c L 2 5 3 N, Nf, Ν "- (1-ethyl-α-2-methoxy-5-sulfamido-pyrrolidylmethyl) -phosphoramide benzoic acid -> pyridine CO-NH-CHp-k.) 3 / ^ V ° CH3 ^ I c2h5 * po ,, h3 H NSO2 / X / phosphoric acid N- (1-ethyl-α-pyrrolidylmethyl) -2-methoxy-5-sulfamidobenzamide The process according to the invention can be carried out in a simple manner as follows: is shown in the following embodiment:
Yhden litran vetoiseen reaktioastiaan asennetaan sekoittaja, lämpömittari ja jäähdyttäjä sekä tiputussuppilo. Tähän reaktioastiaan pannaan 27 g (0,21 moolia) N-etyyli-a-aminometyylipyrrolidiinia ja 560 ml pyridiiniä.A stirrer, thermometer and condenser as well as a dropping funnel are installed in a one-liter reaction vessel. 27 g (0.21 mol) of N-ethyl-α-aminomethylpyrrolidine and 560 ml of pyridine are placed in this reaction vessel.
Tähän liuokseen tiputetaan liuosta, jossa on 6,1 g (0,0*1 moolia) fosforioksikloridia 65 mlrssa pyridiiniä ja lämpötila pysytetään 20°C:ssa. Sekoitetaan 1/2 tunnin ajan ja lisätään sitten 14,8 ml (0,06*» moolia) 2-metoksi-5-sulfamidobentsoehappoa ja keitetään sen jälkeen *1 1/2 tuntia pystyjäähdyttäjän alla.To this solution is added dropwise a solution of 6.1 g (0.0 * 1 mol) of phosphorus oxychloride in 65 ml of pyridine and the temperature is maintained at 20 ° C. Stir for 1/2 hour and then add 14.8 ml (0.06 * mole) of 2-methoxy-5-sulfamidobenzoic acid and then boil for * 1 1/2 hours under reflux.
3 592433 59243
Saatu reaktioseos haihdutetaan vähennetyssä paineessa puoleen tilavuuteensa, suodatetaan ja suodos haihdutetaan kuiviin. Jäännös liuotetaan 200 ml:aan vettä, johon on lisätty 40 ml suolahappoa, jolloin pH-arvo on 1.The reaction mixture obtained is evaporated under reduced pressure to half its volume, filtered and the filtrate is evaporated to dryness. The residue is dissolved in 200 ml of water to which 40 ml of hydrochloric acid have been added, the pH being 1.
Suodatettu liuos pidetään yli yön jääkaapissa, sen jälkeen suodatetaan ja sakka kuivataan kuivauskaapissa lämpötilassa 50°C.The filtered solution is kept in the refrigerator overnight, then filtered and the precipitate is dried in an oven at 50 ° C.
Tämä sakka liuotetaan kuumaan veteen. Pieni liukenematon jäännös suodatetaan kiehuvan kuumasta liuoksesta ja kuuma liuos tehdään ammoniakilla alkaliseksi.·This precipitate is dissolved in hot water. The small insoluble residue is filtered off from the boiling hot solution and the hot solution is made alkaline with ammonia.
Liuoksen annetaan jäähtyä, suodatetaan, pestään vedellä ja kuivataan sakka kuivauskaapissa lämpötilassa 50°C. Tällä tavoin saadaan 7,5 g N-(1-etyyli-a-pyrrolidyylimetyyli)-2-metoksi“5-sulfamido-bentsamidia, jonka sp. on 179°C.The solution is allowed to cool, filtered, washed with water and the precipitate is dried in an oven at 50 ° C. In this way, 7.5 g of N- (1-ethyl-α-pyrrolidylmethyl) -2-methoxy-5-sulfamido-benzamide, m.p. is 179 ° C.
Kun analysoidaan typpipitoisuutta perkloorihapolla (100 %), saadaan typpiarvoksi 12,24 % (laskettu arvo 12,32 %).When the nitrogen content is analyzed with perchloric acid (100%), a nitrogen value of 12.24% (calculated value 12.32%) is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH881372 | 1972-06-13 | ||
| CH881372A CH562790A5 (en) | 1972-06-13 | 1972-06-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59243B FI59243B (en) | 1981-03-31 |
| FI59243C true FI59243C (en) | 1981-07-10 |
Family
ID=4345021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2549/72A FI59243C (en) | 1972-06-13 | 1972-09-15 | PROCEDURE FOR FRAMSTATION OF N- (1-EECL-ALPHA-PYRROLIDYLMETHYL) -2-METOXY-5-SULPHAMIDOBENZAMIDE |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS565733B2 (en) |
| AR (1) | AR193288A1 (en) |
| AT (1) | AT316536B (en) |
| AU (1) | AU464143B2 (en) |
| BE (1) | BE787180A (en) |
| BG (1) | BG20575A3 (en) |
| CA (1) | CA976554A (en) |
| CH (1) | CH562790A5 (en) |
| CS (1) | CS181712B2 (en) |
| DD (1) | DD100249A5 (en) |
| DE (1) | DE2246799A1 (en) |
| EG (1) | EG10796A (en) |
| ES (1) | ES407141A1 (en) |
| FI (1) | FI59243C (en) |
| FR (1) | FR2187782B1 (en) |
| GB (1) | GB1345494A (en) |
| HU (1) | HU165916B (en) |
| IE (1) | IE36719B1 (en) |
| IL (1) | IL40503A (en) |
| IT (1) | IT1034031B (en) |
| LU (1) | LU65860A1 (en) |
| MC (1) | MC938A1 (en) |
| NL (1) | NL7213128A (en) |
| NO (1) | NO140347C (en) |
| OA (1) | OA04167A (en) |
| PL (1) | PL83580B1 (en) |
| RO (1) | RO60562A (en) |
| SE (1) | SE385695B (en) |
| YU (1) | YU35119B (en) |
| ZA (1) | ZA726084B (en) |
| ZM (1) | ZM15172A1 (en) |
-
0
- BE BE787180D patent/BE787180A/en not_active IP Right Cessation
-
1971
- 1971-08-24 AR AR243725A patent/AR193288A1/en active
-
1972
- 1972-06-13 CH CH881372A patent/CH562790A5/xx not_active IP Right Cessation
- 1972-08-07 LU LU65860A patent/LU65860A1/xx unknown
- 1972-08-22 MC MC1007A patent/MC938A1/en unknown
- 1972-08-30 IT IT28620/72A patent/IT1034031B/en active
- 1972-08-31 FR FR7230990A patent/FR2187782B1/fr not_active Expired
- 1972-09-02 OA OA54681A patent/OA04167A/en unknown
- 1972-09-04 GB GB4087072A patent/GB1345494A/en not_active Expired
- 1972-09-06 ZA ZA726084A patent/ZA726084B/en unknown
- 1972-09-07 AU AU46416/72A patent/AU464143B2/en not_active Expired
- 1972-09-12 NO NO3232/72A patent/NO140347C/en unknown
- 1972-09-12 SE SE7211723A patent/SE385695B/en unknown
- 1972-09-14 CA CA151,723A patent/CA976554A/en not_active Expired
- 1972-09-15 FI FI2549/72A patent/FI59243C/en active
- 1972-09-15 CS CS7200006345A patent/CS181712B2/en unknown
- 1972-09-18 HU HUEA921A patent/HU165916B/hu unknown
- 1972-09-19 ZM ZM151/72*UA patent/ZM15172A1/en unknown
- 1972-09-19 IE IE1280/72A patent/IE36719B1/en unknown
- 1972-09-20 PL PL1972157841A patent/PL83580B1/pl unknown
- 1972-09-21 AT AT812672A patent/AT316536B/en not_active IP Right Cessation
- 1972-09-23 DE DE19722246799 patent/DE2246799A1/en active Pending
- 1972-09-25 YU YU2421/72A patent/YU35119B/en unknown
- 1972-09-28 NL NL7213128A patent/NL7213128A/xx unknown
- 1972-09-29 ES ES407141A patent/ES407141A1/en not_active Expired
- 1972-09-29 DD DD165950A patent/DD100249A5/xx unknown
- 1972-09-30 RO RO72382A patent/RO60562A/ro unknown
- 1972-10-04 IL IL40503A patent/IL40503A/en unknown
- 1972-10-12 BG BG21603A patent/BG20575A3/xx unknown
- 1972-12-28 EG EG547/72A patent/EG10796A/en active
-
1973
- 1973-02-01 JP JP1332573A patent/JPS565733B2/ja not_active Expired
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