IL44291A - Preparation of 2-aminoindane derivatives - Google Patents
Preparation of 2-aminoindane derivativesInfo
- Publication number
- IL44291A IL44291A IL44291A IL4429174A IL44291A IL 44291 A IL44291 A IL 44291A IL 44291 A IL44291 A IL 44291A IL 4429174 A IL4429174 A IL 4429174A IL 44291 A IL44291 A IL 44291A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- phenyl
- reaction
- represent
- compound
- Prior art date
Links
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical class C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GPTNZCCQHNGXMS-VOTSOKGWSA-N (e)-4-oxo-4-phenoxybut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1=CC=CC=C1 GPTNZCCQHNGXMS-VOTSOKGWSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
of 2 This invention relates to a process for preparing derivatives of of the formula n is equal to 2 or the group having a or branched and represent a lower radical containing 1 to 3 carbon whereby and may also form together with atom a saturated A is phenyl optionally substituted with one or more lower alkoxy or halogen groups in the meta para position of the phenyl radical and B represents an group of the or different represent a lower a kyl or ydroxyalky radica whereby may also represent whereas and may also form with the attached nitrogen atom a nitrogenous saturated heterocyclic optionally containing a further hetero which may be substituted with lower as well as the acid addition salts of said The compounds of formula are useful for the treatment of heart According to French Patent 2 081 there is known a process for preparing or by reacting aminoindane with sodium amide to form a sodium salt of the which sodium salt is then reacted with a chlorinated According to this the compounds of mula are prepared by a method comprising the two wing steps with a of the formula CI so as to obtain an intermediate a This intermediate product may be isolated or without isolation in the following Reaction of formula with an amine of the following formula In the above formulae to A and B have the above EXAMPLE 1 Preparation of hydrochloride I A mixture of 10 g of and of 25ml of is heated at during 24 After cooling to 5ml of benzene are added and the ture is The residue is dissolved in 50ml of lamine and 70 ml of After addition of of sodium the mixture is refluxed during 24 After tration to the obtained residue is treated with the obtained solution is made alkaline by means of ammonia and extracted with The organic solution is then treated with water and acidified to a pH of After extraction with dichloromethane the aqueous phase is concentrated to dryness and the residue is recrystallized f om methanol of dih drochloride meltin at obtained solution adjusted to a pH of it is possible to recover of the desired 120 EXAMPLES 2 to The compounds of the formula in which and have the meanings indicated in the following table have been prepared by the method described in example 1 using the appropriate of formula and the appropriate amine of formula instead of and diethylamine TABLE A B n R2 of acid addition salt 2 phenyl H ride 3 H 3 xyphenyl de 1 mole 4 H 3 oxalate phenyl 125 128 5 H 3 ride phenyl 6 H 3 phenyl fumarate 138 140 7 phenyl H 3 ride 8 8 phenyl H 4 ride 9 phenyl H 2 C2H5 ride 10 phenyl H 2 CH5 ride insufficientOCRQuality
Claims (1)
1. 44291/2 The embodiment of the invention in v/hich an exclusive property or privilege is claimed are defined as follows : C L A I M S 1.- A process for preparing derivatives of 2-aminoindane of the formula : wherein a straight or branched chain, R1 and R2 represent a lov/er alkyl radical containing 1 to 3 carbon atoms, whereby and R2 may also form together with the adjacent nitrogen atom a nitroge- saturated nous/heterocyclic ring, A is phenyl optionally substituted with one or more hydroxy, lower alkoxy or halogen groups in the ortho, meta and/or para position of the phenyl radical and B represents hydrogen, an alkoxy radical containing 1 to 3 carbon atoms or a group of the formula in which R, and R^, which may be identical or different represent a lower alkyl or hydroxyalkyl radical, whereby R^ may also represent hydrogen, whereas R^ and R^ may also form with the attached nitrogen atom a nitrogenous saturated heterocyclic ring, optionally containing a further hetero atom, which may be substituted with lower alkyl, as well as the acid addition salts of said compound said process comprising the two following steps : ■ - reaction of a N-phenyl-2-arainoindane of the formu with a bromo-chloroalkane of the formula Br-(CH2)n-Cl ' (H ) so as to obtain an intermediate product, i.e. a N-phenyl-N- - reaction of the N-phenyl-N-chloroalkyl=2-aminoin= dane of formula (IV) with an amine of the following formula n, R1 , A and B having the above meanings in the formula (II), (III), (IV) and (V) , the obtained compound of formula I being converted into an acid addition salt, if desired. 2.- A process according to claim 1, in which the. compound of formula (IV) is isolated before the reaction thereof with amine of formula (V).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB998773*[A GB1405444A (en) | 1972-09-18 | 1973-03-01 | 2-aminoindane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44291A0 IL44291A0 (en) | 1974-05-16 |
| IL44291A true IL44291A (en) | 1977-03-31 |
Family
ID=9882457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44291A IL44291A (en) | 1973-03-01 | 1974-02-26 | Preparation of 2-aminoindane derivatives |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5029541A (en) |
| AR (1) | AR208282A1 (en) |
| AT (1) | AT330166B (en) |
| CA (1) | CA997765A (en) |
| CH (1) | CH587796A5 (en) |
| DD (1) | DD110649A5 (en) |
| ES (1) | ES423746A1 (en) |
| HU (1) | HU167911B (en) |
| IL (1) | IL44291A (en) |
| LU (1) | LU69495A1 (en) |
| NL (1) | NL7402731A (en) |
| ZA (1) | ZA741196B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006036936A2 (en) | 2004-09-27 | 2006-04-06 | Bridge Pharma, Inc. | The s-isomer of 2-{2-[n-(2-indanyl)-n-phenylamino]ethyl}piperidine and other dermal anesthetic agents |
| US7592458B2 (en) | 2006-07-21 | 2009-09-22 | Wright George E | Dermal anesthetic compounds and pharmaceutical compositions for inducing local anesthesia and mitigating neuropathic pain |
| US9044482B2 (en) | 2012-08-15 | 2015-06-02 | Asana Biosciences, Llc | Use of aminoindane compounds in treating overactive bladder and interstitial cystitis |
-
1974
- 1974-01-01 AR AR252560A patent/AR208282A1/en active
- 1974-02-22 ZA ZA00741196A patent/ZA741196B/en unknown
- 1974-02-26 IL IL44291A patent/IL44291A/en unknown
- 1974-02-26 JP JP49022702A patent/JPS5029541A/ja active Pending
- 1974-02-27 LU LU69495A patent/LU69495A1/xx unknown
- 1974-02-28 NL NL7402731A patent/NL7402731A/xx not_active Application Discontinuation
- 1974-02-28 CA CA193,775A patent/CA997765A/en not_active Expired
- 1974-02-28 ES ES423746A patent/ES423746A1/en not_active Expired
- 1974-02-28 HU HUCI1457A patent/HU167911B/hu unknown
- 1974-02-28 CH CH283674A patent/CH587796A5/en not_active IP Right Cessation
- 1974-02-28 DD DD176870A patent/DD110649A5/xx unknown
- 1974-03-01 AT AT170474A patent/AT330166B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL44291A0 (en) | 1974-05-16 |
| ZA741196B (en) | 1975-01-29 |
| LU69495A1 (en) | 1974-06-05 |
| ATA170474A (en) | 1975-09-15 |
| NL7402731A (en) | 1974-09-03 |
| CA997765A (en) | 1976-09-28 |
| AR208282A1 (en) | 1976-12-20 |
| ES423746A1 (en) | 1976-05-01 |
| AT330166B (en) | 1976-06-25 |
| CH587796A5 (en) | 1977-05-13 |
| JPS5029541A (en) | 1975-03-25 |
| AU6607374A (en) | 1975-08-28 |
| HU167911B (en) | 1976-01-28 |
| DD110649A5 (en) | 1975-01-05 |
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