GB914503A - Aromatic compounds and methods for their production - Google Patents

Aromatic compounds and methods for their production

Info

Publication number
GB914503A
GB914503A GB4263/61A GB426361A GB914503A GB 914503 A GB914503 A GB 914503A GB 4263/61 A GB4263/61 A GB 4263/61A GB 426361 A GB426361 A GB 426361A GB 914503 A GB914503 A GB 914503A
Authority
GB
United Kingdom
Prior art keywords
acid addition
phenyl
methyl
addition salt
pyrrolidinol
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
GB4263/61A
Inventor
John Frederick Cavalla
Rupert Aleck Selway
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 GB4263/61A priority Critical patent/GB914503A/en
Publication of GB914503A publication Critical patent/GB914503A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/16—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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/12—Oxygen or sulfur atoms

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0914503/IV (b)/1> (wherein Z represents NH2 or NO2) and their acid addition salts, and the preparation thereof by the following processes: (a) reacting 2-methyl-3-phenyl-3-propionyloxypyrrolidine (or an acid addition salt thereof) with a compound of the general formula <FORM:0914503/IV (b)/2> (wherein X represents a halogen atom) or an acid addition salt thereof when Z = NH2; (b) (when Z = NO2) reacting 1-b -(p-nitrophenyl) - ethyl-2-methyl-3-phenyl-3-pyrrolidinol or an acid addition salt thereof with propionic acid or a reactive derivative thereof; or (c) (when Z = NH2) reducing the compound in which Z = NO2, or an acid addition salt thereof; and in each case, if desired, converting a resulting acid addition salt to the free base or vice versa. Optically active compounds can be obtained by using optically active pyrrolidine starting materials or by resolving an optically inactive final product with the aid of an optically active acid. The products are useful as analgesic agents or as intermediates for the preparation of other pyrrolidine derivatives. 1-b -(p-Nitrophenyl)-ethyl-2-methyl-3-phenyl-3-pyrrolidinol is prepared by reacting b -(p-nitrophenyl)-ethyl bromide with 2-methyl-3-phenyl-3-pyrrolidinol, itself prepared by hydrogenolysis of 1 - benzyl - 2 - methyl-3-phenyl-3-pyrrolidinol, which in turn is obtained by alkaline hydrolysis of its propionic ester.
GB4263/61A 1961-02-03 1961-02-03 Aromatic compounds and methods for their production Expired GB914503A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4263/61A GB914503A (en) 1961-02-03 1961-02-03 Aromatic compounds and methods for their production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4263/61A GB914503A (en) 1961-02-03 1961-02-03 Aromatic compounds and methods for their production

Publications (1)

Publication Number Publication Date
GB914503A true GB914503A (en) 1963-01-02

Family

ID=9773815

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4263/61A Expired GB914503A (en) 1961-02-03 1961-02-03 Aromatic compounds and methods for their production

Country Status (1)

Country Link
GB (1) GB914503A (en)

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