GB674246A - Improvements in or relating to amines and aminonitriles and preparation thereof - Google Patents

Improvements in or relating to amines and aminonitriles and preparation thereof

Info

Publication number
GB674246A
GB674246A GB20909/49A GB2090949A GB674246A GB 674246 A GB674246 A GB 674246A GB 20909/49 A GB20909/49 A GB 20909/49A GB 2090949 A GB2090949 A GB 2090949A GB 674246 A GB674246 A GB 674246A
Authority
GB
United Kingdom
Prior art keywords
group
cyclopentenyl
cyclohexenyl
give
treatment
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
GB20909/49A
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB674246A publication Critical patent/GB674246A/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
    • C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—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

Abstract

An aminonitrile of formula <FORM:0674246/IV (b)/1> where R is an aryl thienyl pyridyl or furyl group, Y is an alkylene bridge of 2-3 carbon atoms, -N=B is an aliphatic tertiary amino group, and R1 is cyclopentenyl or cyclohexenyl is prepared by treatment of <FORM:0674246/IV (b)/2> <FORM:0674246/IV (b)/3> where A is cyclopentylidene or cyclohexylidene with the compound Halogen-Y-N=B in the presence of a strong base. The resultant aminonitrile may be heated with a suspension of sodamide in an inert solvent to give an amine <FORM:0674246/IV (b)/4> where the unsatisfied valencies of the carbon atom adjacent to the group R are satisfied by a cyclohexylidene group, a cyclopentylidene group, a cyclohexenyl group and hydrogen, or a cyclopentenyl group and hydrogen (the two different types of compound being tautomeric). The group -N=B may be dialkylamino or a cyclic amino group, e.g. morpholinyl, piperidinyl or pyrrolidinyl. Salts may be formed of the aminonitriles and the amines with acids or lower alkyl esters of strong inorganic or organic sulphonic acids. The group R, when aromatic, may be phenyl, anisyl, tolyl, or naphthyl. The nitriles <FORM:0674246/IV (b)/5> <FORM:0674246/IV (b)/6> (tautomeric forms, both being present to some extent) may be prepared by treatment of a mono-substituted acetonitrile with cyclopentanone or cyclohexanone, or with a D 2- or D 3-cyclopentenyl or cyclohexenyl halide, the latter method giving only compounds of formula <FORM:0674246/IV (b)/7> In the examples, (1) cyclohexanone is condensed with benzyl cyanide to give cyclohexylidenephenylacetonitrile, which is treated with piperidinylethyl chloride to give (p-piperidinoethyl)-D 1 - cyclohexenylphenylacetonitrile, which heated in xylene with sodamide affords 1-piperidino - 3 - phenyl - 3 - (D 1 - cyclohexenyl)-propane; (2) cyclopentanone is condensed with benzyl cyanide to give cyclopentylidenephenylacetonitrile, treatment of which with piperidinoethyl chloride gives b -piperidinoethyl-D 1-cyclopentenylphenylacetonitrile, treatment of which as above affords 1-piperidino-3-phenyl-3-(D 1-cyclopentenyl) propane. Many other examples (13) are given.
GB20909/49A 1948-10-01 1949-08-11 Improvements in or relating to amines and aminonitriles and preparation thereof Expired GB674246A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US674246XA 1948-10-01 1948-10-01

Publications (1)

Publication Number Publication Date
GB674246A true GB674246A (en) 1952-06-18

Family

ID=22075890

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20909/49A Expired GB674246A (en) 1948-10-01 1949-08-11 Improvements in or relating to amines and aminonitriles and preparation thereof

Country Status (1)

Country Link
GB (1) GB674246A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3109845A (en) * 1960-02-04 1963-11-05 Thomae Gmbh Dr K 1-cyclohexyl, 1-cyclohexenyl, 1-furyl, and 1-thienyl, tertiary amino substituted methanes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3109845A (en) * 1960-02-04 1963-11-05 Thomae Gmbh Dr K 1-cyclohexyl, 1-cyclohexenyl, 1-furyl, and 1-thienyl, tertiary amino substituted methanes

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