GB749156A - Improvements in the production of nitrogen-containing carbinols - Google Patents

Abstract

The invention comprises carbinols of the general formula <FORM:0749156/IV(a)/1> (wherein X is a -C­C-, -CH = CH- or -CH2-CH2- group, R is hydrogen or an alkyl group, R1 is hydrogen or an alkyl or cycloalkyl group and R11 is an alkyl or cycloalkyl group, or <FORM:0749156/IV(a)/2> represents the radical of a 5-, 6- or 7-membered saturated cyclic amine), their hydrohalides and metho halides; and their preparation by reacting cyclohexyl phenyl ketone with an acetylene derivative of the general formula <FORM:0749156/IV(a)/3> and, when the formation of the butene or butane derivatives is required, partly or completely hydrogenating the triple bond of the reaction product catalytically. The reaction takes place at atmospheric, increased or reduced pressure, preferably in the presence of ethinylation catalysts such as alkali metal hydroxides, alcoholates and amides, organic bases such as piperidine or diethylamine, hydroxides of heavy metals of the first or second group of the Periodic System such as copper, silver or mercury hydroxides, and the corresponding acetylides. Mixtures of these catalysts can also be used. Solvents are preferably used and heating or cooling may be necessary. Partial hydrogenation to the butene derivatives can be carried out with hydrogen at 200 atmospheres and 100 DEG C. in the presence of Raney iron; use of Raney nickel results in complete hydrogenation to the corresponding butane derivative at 80 DEG C. and 200 atmospheres. Examples describe the preparation of 4-piperidino - 1 - cyclohexyl - 1 - phenyl - 1 - hydroxybutine-(2) and the corresponding butanol-(1), and their hydrochlorides; 4-pyrrolidino-1-cyclohexyl - 1 - phenyl - 1 - hydroxy - butine - (2); 4 - hexamethyleneimino - 1 - cyclohexyl - 1 - phenyl - 1 - hydroxybutine - (2) and its hydrochloride; and 4 - diethylamino - 1 - cyclohexyl - 1 - phenyl - 1 - hydroxybutine - (2) and its methiodide, and the methiodides of the corresponding butene-(2) and butane derivatives. The products are useful as spasmolytics. Aminopropines are obtained by reacting acetylene with alpha-hydroxy-alkylamines in the presence of heavy metals of Groups 1 and 2 of the Periodic System. 2-Aminobutines-(3) are obtained by reacting acetylene with primary or secondary amines in the presence of acetylenides of heavy metals of Groups 1 and 2 of the Periodic System. Specification 724,759 is referred to.