GB966562A - Amine compounds and means of producing the same - Google Patents
Amine compounds and means of producing the sameInfo
- Publication number
- GB966562A GB966562A GB1247761A GB1247761A GB966562A GB 966562 A GB966562 A GB 966562A GB 1247761 A GB1247761 A GB 1247761A GB 1247761 A GB1247761 A GB 1247761A GB 966562 A GB966562 A GB 966562A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- methyl
- nitrovinyl
- indole
- reacting
- 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.)
- Expired
Links
- -1 Amine compounds Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- VKRJAGSKSCDGEI-UHFFFAOYSA-N 5-fluoro-3-hydroxy-3-(2-oxopropyl)-1h-indol-2-one Chemical compound C1=C(F)C=C2C(CC(=O)C)(O)C(=O)NC2=C1 VKRJAGSKSCDGEI-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 abstract 1
- YUAJKGBLPVLADK-UHFFFAOYSA-N 5-fluoro-1h-indole-3-carbaldehyde Chemical compound FC1=CC=C2NC=C(C=O)C2=C1 YUAJKGBLPVLADK-UHFFFAOYSA-N 0.000 abstract 1
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- 230000003555 analeptic effect Effects 0.000 abstract 1
- 239000002830 appetite depressant Substances 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
Classifications
-
- 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
- C07D209/16—Tryptamines
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises 5-fluoro-a -methyl-tryptamine and its acid addition salts, and the preparation thereof by (a) reducing 5-fluoro-3-(21-methyl-21-nitrovinyl)-indole by reaction in the presence of an anhydrous non-hydroxylic organic solvent with lithium aluminium hydride or with a complex oxidisable metal borohydride in the presence of aluminium chloride, and decomposition of the resulting complex with water or an aqueous medium, or (b) treating 5-fluoro-3-(21-methyl-21-nitrovinyl)-indole with iron and acetic acid in the presence of water and an inert water miscible organic solvent and subjecting the resulting 3-(5-fluoro)-indolylacetone to reductive amination, or (c) reacting 3-acetonyl-3-hydroxy-5-fluoro-oxindole with hydroxylamine and reducing the resulting oxime by the method of (a), and isolating the products as free bases or acid addition salts. The products are useful as analeptic and anorexic agents, or as intermediates for preparing other compounds. 5- Fluoro -3- (21- methyl -21- nitrovinyl)-indole is prepred by reacting 5-fluoroindole with dimethylformamide and phosphorus oxychloride followed by caustic soda to form 5-fluoroindole-3-aldehyde and refluxing this with nitroethane in the presence of ammonium acetate. 3- Acetonyl -3- hydroxy -5- fluoro-oxindole is prepared by reacting 5-fluoroisatin with acetone in the presence of diethylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1247761A GB966562A (en) | 1961-04-06 | 1961-04-06 | Amine compounds and means of producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1247761A GB966562A (en) | 1961-04-06 | 1961-04-06 | Amine compounds and means of producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966562A true GB966562A (en) | 1964-08-12 |
Family
ID=10005307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1247761A Expired GB966562A (en) | 1961-04-06 | 1961-04-06 | Amine compounds and means of producing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB966562A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5559246A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc. | Indole derivatives |
| US5559129A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| US5607951A (en) * | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
| US5849739A (en) * | 1993-08-31 | 1998-12-15 | Pfizer Inc. | 5-arylindole derivatives |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| US6110940A (en) * | 1994-08-27 | 2000-08-29 | Pfizer Inc. | Salts of an anti-migraine indole derivative |
| JP2004534816A (en) * | 2001-06-21 | 2004-11-18 | シグマ−タウ・インドゥストリエ・ファルマチェウチケ・リウニテ・ソシエタ・ペル・アチオニ | 5-halo-tryptamine derivatives for use as ligands for 5-HT6 and / or 5-HT7 serotonin receptors |
| CN114230507A (en) * | 2021-12-31 | 2022-03-25 | 阜阳欣奕华制药科技有限公司 | A kind of preparation method of 5-methoxytryptamine |
-
1961
- 1961-04-06 GB GB1247761A patent/GB966562A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5559246A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc. | Indole derivatives |
| US5559129A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| US5607951A (en) * | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
| US5849739A (en) * | 1993-08-31 | 1998-12-15 | Pfizer Inc. | 5-arylindole derivatives |
| US6093822A (en) * | 1993-08-31 | 2000-07-25 | Pfizer Inc. | 5-arylindole derivatives |
| US6110940A (en) * | 1994-08-27 | 2000-08-29 | Pfizer Inc. | Salts of an anti-migraine indole derivative |
| US6380226B1 (en) | 1994-08-27 | 2002-04-30 | Pfizer Inc | Salts of an anti-migraine indole derivatives |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| JP2004534816A (en) * | 2001-06-21 | 2004-11-18 | シグマ−タウ・インドゥストリエ・ファルマチェウチケ・リウニテ・ソシエタ・ペル・アチオニ | 5-halo-tryptamine derivatives for use as ligands for 5-HT6 and / or 5-HT7 serotonin receptors |
| CN114230507A (en) * | 2021-12-31 | 2022-03-25 | 阜阳欣奕华制药科技有限公司 | A kind of preparation method of 5-methoxytryptamine |
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