Patent GB-964712-A (GB)
Title: Acetamide derivatives
IPC: C07C233/12
Filed: 1961-03-30
Abstract: The invention comprises compounds of the formula: <FORM:0964712/C1/1> (wherein R is lower alkyl, R1 is lower alkyl or lower alkenyl; each R11 is hydrogen, halogen, halomethyl, lower alkyl, lower alkoxy, hydroxy, nitro, amino, cyano or lower alkanoyloxy; Y is lower alkylene separating the nitrogens by at least 2 carbon atoms; Z is lower alkylene, oxolower alkylene or ethenylene; and R111 is phenyl, R11-substituted phenyl, thienyl, furyl or pyridyl, the word "lower" referring to groups containing at most 7 carbon atoms); and acid-addition salts and quaternary ammonium derivatives thereof; and their preparation by (1) reacting an a -halodiphenylacetyl halide with the appropriate diamine and treating the product with the appropriate alkanol or alkoxide ROA, where A is hydrogen or an alkali metal; or (2) reacting an a -alkoxy-N-alkyl-N-(alkylaminoalkyl)-diphenylacetamide with an R111-Z-CH2-halide.  In examples (1) and (2) 2-methylaminoethanol and 2-bromoethylbenzene are condensed to give 2-(N-methyl-N-phenethylamino)-ethanol, this with thionyl chloride gives 2-(N-methyl-N-phenethylamino)-ethyl chloride hydrochloride, this with methylamine gives N,N1-dimethyl-N-phenethylethylenediamine, and this with a -chlorodiphenylacetyl chloride and ethanol gives 2-ethoxy-N-methyl-N-[2-(N1-methyl - N1 - phenethylamino)-ethyl]-2,2-diphenylacetamide hydrochloride, which may also be prepared by reacting a -chlorodiphenylacetyl chloride with methylamine and ethanol to give 2-ethoxy-N-methyl-2,2-diphenylacetamide and then reacting this with 2-(methylphenethylamino)-ethyl chloride; (3) 2,2,-bis-(o-chlorophenyl)-2-ethoxy-N-methyl-N-[2 -(methylphenethylamino)-ethyl]-acetamide hydrochloride is prepared by the method of (1); (4) and (5), 2-(N-benzyl-N-methylamino)-ethyl chloride hydrochloride and methylamine give N-benzyl-N,N1-dimethylethylenediamine, this with a -dichlorodiphenylacetyl chloride and ethanol gives N-[2-(N1-benzyl-N1-methylamino)-ethyl] -2-ethoxy-N-methyl-2,2-diphenylacetamide hydrochloride this on hydrogenolysis gives 2-ethoxy-N-methyl-N-(2-methylaminoethyl) -2,2-diphenylacetamide hydrochloride, this with p-nitrophenethyl bromide gives N-{2-[N1-(p-nitrophenethyl)-N1-methylamino] -ethyl}-2-ethoxy-N-methyl-2, 2-diphenylacetamide hydrochloride and this on reduction gives the corresponding p-amino compound; (6) to (10) the method of (4) is used to prepare other products of the above general formula; (11) 2-allylaminoethanol and 2-bromoethylbenzene give 2-(N-allyl-N-phenethylamino)-ethanol, this with thionyl chloride gives 2-(N-allyl-N-phenethylamino)-ethy chloride hydrochloride, this with ethylamine gives N-allyl-N1-ethyl-N-phenethylenediamine, and this with 2-chloro-2,2-bis-(m-trifluoromethylphenyl)-acetyl chloride and ethanol gives 2-ethoxy-N-ethyl-N-[2-(N1-allyl-N1-phenethylamino) -ethyl]-2, 2-bis-(m-trifluoromethylphenyl)-acetamide hydrochloride; (12) and (13) other products of the above general formula are prepared by similar methods, 2-ethoxy-N-methyl-N-[2-(N1-methyl-N1-phenethylamino) -ethyl]-2-(m-hydroxyphenyl)-2-phenylaectamide hydrochloride being obtained by hydrogen bromide cleavage of the corresponding m-methoxy-phenyl compound.  A list of salt-forming organic and inorganic acids and quaternising agents is also provided.  U.S.A. Specification 2,862,965 is referred to.