HUP9702472A2 - Process for producing allyl-amine derivative and salt thereof - Google Patents
Process for producing allyl-amine derivative and salt thereofInfo
- Publication number
- HUP9702472A2 HUP9702472A2 HU9702472A HUP9702472A HUP9702472A2 HU P9702472 A2 HUP9702472 A2 HU P9702472A2 HU 9702472 A HU9702472 A HU 9702472A HU P9702472 A HUP9702472 A HU P9702472A HU P9702472 A2 HUP9702472 A2 HU P9702472A2
- Authority
- HU
- Hungary
- Prior art keywords
- ene
- salt
- methyl
- base
- yne
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title abstract 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- ZIXABMZBMHDFEZ-UHFFFAOYSA-N 1-chloro-6,6-dimethylhept-2-en-4-yne Chemical compound CC(C)(C)C#CC=CCCl ZIXABMZBMHDFEZ-UHFFFAOYSA-N 0.000 abstract 3
- MOWPBNFGGOHZRW-UHFFFAOYSA-N 6,6-dimethylhept-1-en-4-yn-3-ol Chemical compound CC(C)(C)C#CC(O)C=C MOWPBNFGGOHZRW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
New preparation of (E)-N-methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-ene-4-ynyl-1-amine (I) and its salt involves reacting 1-chloro-6,6-dimethyl-hept-2-ene-4-yne with N-methyl-1-naphthalenemethylamine in an aliphatic ketone-type solvent in the presence of a base. Preparation of (E)-N-methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-ene-4-ynyl-1-amine (I) and its acid addition salt involves reacting a 1-chloro-6,6-dimethyl-hept-2-ene-4-yne (IIIb) with N-methyl-1-naphthalenemethylamine (II) in an aliphatic ketone-type solvent in the presence of a base and optionally iodide salt catalyst. (IIIb) contains E and Z isomers of ratio 3.3 - 3.4:1 and is obtained by the reaction of 3-hydroxy-6,6-dimethyl-hept-1-ene-4-yne (IV) with hydrochloric acid. (I) is in base form and has ratio of isomers 3.3 - 3.4:1 is converted by aqueous HCl directly to the hydrochloride salt, the precipitated hydrochloride of the E-isomer is separated, optionally the base is liberated and converted to the acid addition salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9702472A HU223057B1 (en) | 1997-12-15 | 1997-12-15 | Process for producing allyl-amine derivative and salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9702472A HU223057B1 (en) | 1997-12-15 | 1997-12-15 | Process for producing allyl-amine derivative and salts thereof |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HU9702472D0 HU9702472D0 (en) | 1998-03-02 |
| HUP9702472A2 true HUP9702472A2 (en) | 2000-02-28 |
| HUP9702472A3 HUP9702472A3 (en) | 2000-06-28 |
| HU223057B1 HU223057B1 (en) | 2004-03-01 |
Family
ID=89995869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9702472A HU223057B1 (en) | 1997-12-15 | 1997-12-15 | Process for producing allyl-amine derivative and salts thereof |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HU223057B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012101044A1 (en) * | 2011-01-24 | 2012-08-02 | Bayer Cropscience Ag | Method for producing 2,2-difluoroethylamine starting from 2,2-difluoro-1-chloroethane |
-
1997
- 1997-12-15 HU HU9702472A patent/HU223057B1/en active IP Right Grant
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012101044A1 (en) * | 2011-01-24 | 2012-08-02 | Bayer Cropscience Ag | Method for producing 2,2-difluoroethylamine starting from 2,2-difluoro-1-chloroethane |
| US8580973B2 (en) | 2011-01-24 | 2013-11-12 | Bayer Cropscience Ag | Process for the preparation of 2,2-difluoroethylamine |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9702472A3 (en) | 2000-06-28 |
| HU223057B1 (en) | 2004-03-01 |
| HU9702472D0 (en) | 1998-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HFG4 | Patent granted, date of granting |
Effective date: 20040114 |
|
| HC9A | Change of name, address |
Owner name: RICHTER GEDEON NYRT., HU Free format text: FORMER OWNER(S): RICHTER GEDEON VEGYESZETI GYAR RT., HU |