Ch2cn

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-bicyclohexanecar-boxylic acid (14.1.34), which undergoes transesterification by 2-diethylaminoethanol in the presence of sodium [25].

cn cn

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. Synonyms of this drug are anaspaz, bentyl, dibent, and formulex.

Oxybutynin: Oxybutynin, 4-diethylamino-2-butynylic ester a-phenylclohexaneglycolic acid (14.1.35), is synthesized either by a Mannich reaction using propargyl ester of a-phenyl-a-cyclohexaneglycolic acid, paraform and diethylamine, or transesterification of the methyl ester of a-phenyl-a-cyclohexaneglycolic acid using 1-acetoxy-4-diethylamino-2-butene in the presence of sodium methoxide [26].

C-C00-CH2-CECH + CH20 + H-N < C-C00-CH2-CEC-CH2—N

0H C2H5 0H C2H5

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