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GB846675A - Process for the production of a tryptamine derivative - Google Patents

Process for the production of a tryptamine derivative

Info

Publication number
GB846675A
GB846675A GB12493/59A GB1249359A GB846675A GB 846675 A GB846675 A GB 846675A GB 12493/59 A GB12493/59 A GB 12493/59A GB 1249359 A GB1249359 A GB 1249359A GB 846675 A GB846675 A GB 846675A
Authority
GB
United Kingdom
Prior art keywords
fluorotryptamine
fluoro
nitro
alkali metal
acid
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
GB12493/59A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie SA
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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB846675A publication Critical patent/GB846675A/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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

The invention comprises 6-fluorotryptamine and its acid addition salts, such as the picrate, hydrochloride, and sulphate, and the production of 6-fluorotryptamine by diazotising 2-nitro-4-aminotoluene, treating with fluoboric acid, and heating to prepare 2-nitro-4-fluorotoluene, condensing with ethyl oxalate in the presence of an alkali metal ethylate and isolating the alkali metal salt of ethyl 41-fluoro-21-nitro-phenyl pyruvate, treating with acid to obtain the ester, reducing, and cyclising to form ethyl 6-fluoro-indole-6-carboxylate by the action of a reducing agent in an acid medium; the indole derivative is saponified and decarboxylated to 6-fluoroindole, which is condensed with dimethylamine and formaldehyde to form 6-fluorogramine, which is isolated, quaternised with methyl sulphate and reacted with an alkali metal cyanide; the 6-fluoro-3-indolyl-acetonitrile is isolated and catalytically hydrogenated to yield 6-fluorotryptamine. 6-fluorotryptamine is an intermediate in the synthesis of compounds of the reserpine series, and is an antimetabolite for tryptophane; it may be used when the microbiological conversion of tryptophane to indole is to be avoided, e.g. in pathological intestinal fermentations.
GB12493/59A 1958-04-18 1959-04-13 Process for the production of a tryptamine derivative Expired GB846675A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR846675X 1958-04-18

Publications (1)

Publication Number Publication Date
GB846675A true GB846675A (en) 1960-08-31

Family

ID=9313453

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12493/59A Expired GB846675A (en) 1958-04-18 1959-04-13 Process for the production of a tryptamine derivative

Country Status (1)

Country Link
GB (1) GB846675A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011076212A3 (en) * 2009-12-23 2011-08-11 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011076212A3 (en) * 2009-12-23 2011-08-11 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent
CN102656146A (en) * 2009-12-23 2012-09-05 H.隆德贝克有限公司 Processes for the manufacture of a pharmaceutically active agent
JP2013515683A (en) * 2009-12-23 2013-05-09 ハー・ルンドベック・アクチエゼルスカベット Method for producing pharmaceutically active agent
US8461353B2 (en) 2009-12-23 2013-06-11 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent
CN103694161A (en) * 2009-12-23 2014-04-02 H.隆德贝克有限公司 Processes for the manufacture of a pharmaceutically active agent
US8901318B2 (en) 2009-12-23 2014-12-02 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent
CN102656146B (en) * 2009-12-23 2014-12-17 H.隆德贝克有限公司 Processes for the manufacture of a pharmaceutically active agent
AU2010335659B2 (en) * 2009-12-23 2015-05-21 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent
EA021440B1 (en) * 2009-12-23 2015-06-30 Х. Лундбекк А/С Process for the manufacture of a pharmaceutically active agent
CN103694161B (en) * 2009-12-23 2015-09-09 H.隆德贝克有限公司 Process for the manufacture of pharmaceutically active agents
JP2016117734A (en) * 2009-12-23 2016-06-30 ハー・ルンドベック・アクチエゼルスカベット Method for the manufacture of pharmaceutically active agent
US9382205B2 (en) 2009-12-23 2016-07-05 H. Lundbeck A/S Processes for the manufacture of a pharmaceutically active agent

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