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GB966562A - Amine compounds and means of producing the same - Google Patents

Amine compounds and means of producing the same

Info

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
Application number
GB1247761A
Inventor
Lydia Kruszynska
Henry Oswald Jackson Collier
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB1247761A priority Critical patent/GB966562A/en
Publication of GB966562A publication Critical patent/GB966562A/en
Expired legal-status Critical Current

Links

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.
GB1247761A 1961-04-06 1961-04-06 Amine compounds and means of producing the same Expired GB966562A (en)

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)

* Cited by examiner, † Cited by third party
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 Preparation method of 5-methoxytryptamine

Cited By (14)

* Cited by examiner, † Cited by third party
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
JP4683839B2 (en) * 2001-06-21 2011-05-18 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 used 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 Preparation method of 5-methoxytryptamine

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