GB807876A - Manufacture of indole derivatives - Google Patents

Manufacture of indole derivatives

Info

Publication number
GB807876A
GB807876A GB440656A GB440656A GB807876A GB 807876 A GB807876 A GB 807876A GB 440656 A GB440656 A GB 440656A GB 440656 A GB440656 A GB 440656A GB 807876 A GB807876 A GB 807876A
Authority
GB
United Kingdom
Prior art keywords
hydrochloride
aminopropyl
methoxy
formula
radicals
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
GB440656A
Inventor
Edwin Harry Paterson Young
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB440656A priority Critical patent/GB807876A/en
Publication of GB807876A publication Critical patent/GB807876A/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

Landscapes

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

Abstract

The invention comprises indole derivatives of the formula <FORM:0807876/IV (b)/1> and salts thereof, wherein R represents hydrogen or a C1-4 alkyl radical and the ring A may optionally be substituted by halogen, C1-4 alkyl radicals, C1-4 alkoxy radicals or aralkoxy radicals, but excluding the known compounds 5-benzyloxy-, 5-methoxy-, 5-ethoxy-, 6-methoxy-, 7-methoxy- and 7-methyl-tryptamine, 3-b -aminopropylindole and 3-b -aminobutylindole. Both the new and the known compounds of the above general formula are prepared by reducing compounds of the formula <FORM:0807876/IV (b)/2> with lithium aluminium hydride. The reaction is preferably conducted by heating the reactants in the presence of a solvent such as tetrahydrofuran or diethylether. The examples describe the preparation of tryptamine and the hydrochloride and picrate thereof, 5-chlorotryptamine hydrochloride, 6 - benzyloxytryptamine hydrochloride, 5 - benzyloxytryptamine hydrochloride, 3 - b - aminopropylindole hydrochloride, 3 - b - aminobutylindole hydrochloride, 3 - b - aminoethyl - 5 - methylindole hydrochloride, 3 - b - aminopropyl - 5 - methylindole hydrochloride, 3 - b - aminopropyl - 5 - methoxyindole hydrochloride, 3 - (b - aminopropyl)-5 - benzyloxyindole hydrochloride and succinate and 3 - (b - aminobutyl) - 5 - benzyloxyindole hydrochloride. Specifications 807,875 and 807,877 are referred to.
GB440656A 1956-02-13 1956-02-13 Manufacture of indole derivatives Expired GB807876A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB440656A GB807876A (en) 1956-02-13 1956-02-13 Manufacture of indole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB440656A GB807876A (en) 1956-02-13 1956-02-13 Manufacture of indole derivatives

Publications (1)

Publication Number Publication Date
GB807876A true GB807876A (en) 1959-01-21

Family

ID=9776598

Family Applications (1)

Application Number Title Priority Date Filing Date
GB440656A Expired GB807876A (en) 1956-02-13 1956-02-13 Manufacture of indole derivatives

Country Status (1)

Country Link
GB (1) GB807876A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1150983B (en) * 1959-06-26 1963-07-04 Roussel Uclaf Process for the preparation of 5-methoxy-ª-ethyl-tryptamine and its salts
US3168526A (en) * 1960-04-20 1965-02-02 Upjohn Co Derivatives of 3-(2-nitroethyl)-indole
US3282959A (en) * 1961-04-06 1966-11-01 Parke Davis & Co 7-chloro-alpha-methyltryptamine derivatives
US3296072A (en) * 1962-06-11 1967-01-03 Upjohn Co Method of treating mental depression
US3365464A (en) * 1962-06-11 1968-01-23 Upjohn Co 7-alkyl-3-(2-aminobutyl) indoles
CN110746340A (en) * 2019-11-07 2020-02-04 上海易恩化学技术有限公司 Synthetic method of 5-methoxy-2-methyltryptamine

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1150983B (en) * 1959-06-26 1963-07-04 Roussel Uclaf Process for the preparation of 5-methoxy-ª-ethyl-tryptamine and its salts
US3168526A (en) * 1960-04-20 1965-02-02 Upjohn Co Derivatives of 3-(2-nitroethyl)-indole
US3282959A (en) * 1961-04-06 1966-11-01 Parke Davis & Co 7-chloro-alpha-methyltryptamine derivatives
US3296072A (en) * 1962-06-11 1967-01-03 Upjohn Co Method of treating mental depression
US3365464A (en) * 1962-06-11 1968-01-23 Upjohn Co 7-alkyl-3-(2-aminobutyl) indoles
CN110746340A (en) * 2019-11-07 2020-02-04 上海易恩化学技术有限公司 Synthetic method of 5-methoxy-2-methyltryptamine

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