uses
Dicyclomine inhibits muscarinic action of acethylcholine on postganglionic parasympathetic effector regions. It is used in combination with other drugs for treating stomach ulcers, colic in children, and for treating irritable bowel syndrome.
Synthetic Method
Dicyclomine, diethylaminoethyl ester of 1-cyclohexylcyclohexanecarboxylic acid (14.1.32), is synthesized in two different ways. According to the first, benzyl cyanide undergoes alkylation by 1,5-dibromopentane, which forms 1-cyano-1-phenyl-cyclohexane (14.1.29). This undergoes alcoholysis, which gives the ethyl ester of 1-phenyl-1-cyclohexanecarboxylic acid (14.1.30), which undergoes transesterification using 2-diethylaminoethanol in the presence of sodium as an alcoholic component, giving the 2-diethylaminoethyl ester of 1-phenylcyclohexanecarboxylic acid (14.1.31), the phenyl group of which is reduced to a cyclohexyl group using hydrogen over platinum oxide.
The second method for the synthesis of dicyclomine is started from cyanocyclohexane, which undergoes alkylation by cyclohexylbromide, forming 1-cyanobicyclohexane (14.1.33). This undergoes alcoholysis, forming the ethyl ester of 1-bicyclohexanecarboxylic acid (14.1.34), which undergoes transesterification by 2-diethylaminoethanol in the presence of sodium.
Uses
Dicyclomine inhibits muscarinic action of acethylcholine on postganglionic parasympathetic effector regions. It is used in combination with other drugs for treating stomach
ulcers, colic in children, and for treating irritable bowel syndrome.
Synthesis
Dicyclomine, diethylaminoethyl ester of 1-cyclohexylcyclohexanecarboxylic
acid (14.1.32), is synthesized in two different ways. According to the first, benzyl cyanide
undergoes alkylation by 1,5-dibromopentane, which forms 1-cyano-1-phenyl-cyclohexane
(14.1.29). This undergoes alcoholysis, which gives the ethyl ester of 1-phenyl-1-cyclohexanecarboxylic acid (14.1.30), which undergoes transesterification using 2-diethylaminoethanol
in the presence of sodium as an alcoholic component, giving the 2-diethylaminoethyl ester of
1-phenylcyclohexanecarboxylic acid (14.1.31), the phenyl group of which is reduced to a
cyclohexyl group using hydrogen over platinum oxide [24,25].
The second method for the synthesis of dicyclomine is started from cyanocyclohexane,
which undergoes alkylation by cyclohexylbromide, forming 1-cyanobicyclohexane
(14.1.33). This undergoes alcoholysis, forming the ethyl ester of 1-bicyclohexanecarboxylic acid (14.1.34), which undergoes transesterification by 2-diethylaminoethanol in
the presence of sodium [25].
