GB770370A - Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor - Google Patents

Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor

Info

Publication number
GB770370A
GB770370A GB960155A GB960155A GB770370A GB 770370 A GB770370 A GB 770370A GB 960155 A GB960155 A GB 960155A GB 960155 A GB960155 A GB 960155A GB 770370 A GB770370 A GB 770370A
Authority
GB
United Kingdom
Prior art keywords
methyl
benzyloxyindolyl
benzyloxy
ester
ethylcarbamate
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
GB960155A
Inventor
Romeo Justoni
Raffaele Pessina
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.)
Francesco Vismara SpA
Original Assignee
Francesco Vismara SpA
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 Francesco Vismara SpA filed Critical Francesco Vismara SpA
Priority to GB960155A priority Critical patent/GB770370A/en
Publication of GB770370A publication Critical patent/GB770370A/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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises (1) the compound 5-benzyloxy-indole-3-b -propionazide, (2) the preparation therefrom of b -[3-(5-benzyloxyindolyl)]-ethylcarbami esters with alkanols of up to 5 carbon atoms and with benzyl alcohol, and (3) the following synthesis of 5-hydroxytryptamine using the above as intermediates: 5 - benzyloxy - 2 - carboxyindole - 3 - b - propionic acid (see Specification 766,036) is decarboxylated by heating to 190-230 DEG C., the product esterified with an alkanol of up to 5 carbon atoms and the ester reacted with hydrazine hydrate to give 5-benzyloxy-indole-3-b -propionhydrazide; the latter is converted into the azide by treatment with sodium nitrite and acid in the presence of ether, an aliphatic alcohol of 4-5 carbon atoms, benzene or a methyl-substituted benzene as solvent; the azide is heated to 60-140 DEG C. with the appropriate esterifying alcohol (if not already present as solvent) to form the b -[3-(5-benzyloxyindolyl)]-ethylcarbamic ester (via the isocyanate, not isolated); finally 5-hydroxytryptamine is obtained from the carbamic ester by catalytic hydrogenolysis and acid hydrolysis simultaneously or successively in either order. The hydrogenolysis is preferably carried out with a palladium catalyst in alcoholic solution, and if hydrolysis precedes this the 5-benzyloxytryptamine may be isolated as its benzoate or salicylate. Examples show the preparation of the following :-(1) 5-benzyloxy-indole-3-b -propionic acid and its methyl ester, hydrazide and azide, methyl b -[3-(5-benzyloxyindolyl)]-ethylcarbamate, methyl b -[3-(5-hydroxyindolyl)]-ethylcarbamate, methyl b - [3 - (5 - hydroxyindolyl)]-ethylcarbamate and 5-hydroxytryptamine (isolated as picrate); (2) as in (1) but proceeding via 5-benzyloxy-tryptamine salicylate or benzoate; (3) as in (1) but forming the ethyl esters instead of the methyl esters; (4) as in (1) but converting the azide to benzyl b -[3-(5-benzyloxyindolyl)] - ethylcarbamate and the latter directly to 5-hydroxytryptamine, isolated as picrate or as the double sulphate with creatinine. The isoamyl ester of b -[3-(5-benzyloxyindolyl)]-ethylcarbamic acid is also mentioned.
GB960155A 1955-04-01 1955-04-01 Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor Expired GB770370A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB960155A GB770370A (en) 1955-04-01 1955-04-01 Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB960155A GB770370A (en) 1955-04-01 1955-04-01 Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor

Publications (1)

Publication Number Publication Date
GB770370A true GB770370A (en) 1957-03-20

Family

ID=9875133

Family Applications (1)

Application Number Title Priority Date Filing Date
GB960155A Expired GB770370A (en) 1955-04-01 1955-04-01 Improvements in or relating to the preparation of 5-hydroxy-tryptamine and intermediates therefor

Country Status (1)

Country Link
GB (1) GB770370A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2943093A (en) * 1960-06-28 Process of purifying tryptamine com-
US2947757A (en) * 1956-02-21 1960-08-02 Francesco Vismara Societa Per Process for preparing 5-hydroxy-tryptamine through new intermediates
US7125906B2 (en) 2002-04-03 2006-10-24 Astrazeneca Ab Indole derivatives having anti-angiogenetic activity

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2943093A (en) * 1960-06-28 Process of purifying tryptamine com-
US2947757A (en) * 1956-02-21 1960-08-02 Francesco Vismara Societa Per Process for preparing 5-hydroxy-tryptamine through new intermediates
US7125906B2 (en) 2002-04-03 2006-10-24 Astrazeneca Ab Indole derivatives having anti-angiogenetic activity

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