GB617709A - Improvements in and relating to the preparation of heterocyclic compounds - Google Patents

Improvements in and relating to the preparation of heterocyclic compounds

Info

Publication number
GB617709A
GB617709A GB3135446A GB3135446A GB617709A GB 617709 A GB617709 A GB 617709A GB 3135446 A GB3135446 A GB 3135446A GB 3135446 A GB3135446 A GB 3135446A GB 617709 A GB617709 A GB 617709A
Authority
GB
United Kingdom
Prior art keywords
methoxy
piperidine
hydroxy
benzoxy
give
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
GB3135446A
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.)
SAMUEL WILKONSON
Wellcome Foundation Ltd
Original Assignee
SAMUEL WILKONSON
Wellcome Foundation 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 SAMUEL WILKONSON, Wellcome Foundation Ltd filed Critical SAMUEL WILKONSON
Priority to GB3135446A priority Critical patent/GB617709A/en
Publication of GB617709A publication Critical patent/GB617709A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Heterocyclic compounds of the general formula <FORM:0617709/IV(b)/1> where R1 is a phenyl or substituted phenyl radical R1 is hydrogen or an alkoxy radical, R3 is hydrogen or an alkyl radical and <FORM:0617709/IV(b)/2> denotes the residue of a heterocyclic compound containing a cyclic secondary nitrogen atom, are prepared by treating an aroyl acid chloride R1COCl with the appropriate hydroxy-a -haloketone to give the ester <FORM:0617709/IV(b)/3> where Z is a halogen atom, and treating this with a heterocyclic amine to obtain the required product. Preferably an esterified hydroxy-a -chloroketone is treated with two equivalents of the heterocyclic amine. Alternatively the compounds may also be obtained by treating a hydroxy-a -haloketone first with the amine and then with the aroyl acid chloride. Preferably a hydroxy-a -chloroketone is treated with three or more equivalents of the heterocyclic amine in the presence of a small amount of potassium iodide. The bases are normally employed as their hydrochlorides or other acid salts. In examples: (1) 4-benzoxy-o -chloroacetophenone is treated with piperidine to give N-(p-benzoxy-phenacyl) piperidine; (2) 3-methoxy-4-hydroxy-o -chloroacetophenone is treated with piperidine and the product is benzoylated to give N-[(3-methoxy-4-benzoxy) phenacyl] piperidine which is isolated as the hydrochloride; (3) 3-methoxy - 4 - hydroxy - o - chloroacetophenone is treated with benzoyl chloride and the product is reacted with piperidine to give the product of (2); (4) 3-methoxy-4-hydroxy-o -chloroacetophenone reacts with anisoyl chloride followed by piperidine to give N-[3-methoxy-4-anisoxy)-phenacyl] piperidine hydrochloride; (5) 3-methoxy-4-benzoxy-o -chloroacetophenone reacts with tetrahydroquinoline to give N-[(3-methoxy - 4 - benzoxy)phenacetyl]tetrahydroquinoline; (6) by using morpholine in place of tetrahydroquinoline in the process of (5) N-[(3 - methoxy - 4 - benzoxy)phenacetyl)]tetra-hydroquinoline is obtained. By similar methods N - (3 - benzoxyphenacyl) - piperidine hydrochloride and N-(3-benzoxyphenacyl)-morpholine hydrochloride may be obtained.
GB3135446A 1946-10-22 1946-10-22 Improvements in and relating to the preparation of heterocyclic compounds Expired GB617709A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3135446A GB617709A (en) 1946-10-22 1946-10-22 Improvements in and relating to the preparation of heterocyclic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3135446A GB617709A (en) 1946-10-22 1946-10-22 Improvements in and relating to the preparation of heterocyclic compounds

Publications (1)

Publication Number Publication Date
GB617709A true GB617709A (en) 1949-02-10

Family

ID=10321862

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3135446A Expired GB617709A (en) 1946-10-22 1946-10-22 Improvements in and relating to the preparation of heterocyclic compounds

Country Status (1)

Country Link
GB (1) GB617709A (en)

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