P. Janssen
1960
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Abstract
This chapter discusses the methods of synthesis of 3:3-diphenylpropylamines. The treatment of basic nitriles with excess sodamide leads to the replacement of the cyano group by hydrogen. The preparation of 3:3-diphenylpropylamines by this method gives excellent yield. The dehydration and reduction of basic tertiary alcohols in one step, using red phosphorus and hydriodic acid, or in two steps, using dehydration in acid medium followed by catalytic hydrogenation, also gives 3:3-diphenylpropylamines. Another method is the condensation of a tertiary aminoethylchloride with sodium or potassium diphenylmethide. The less important methods of synthesis include the reductive condensation of 2:2-diphenylpropionaldehyde and a secondary amine; the condensation of 3:3-diphenylpropylchloride with a secondary amine; and the decarboxylation of aminoacids. All known 3:3-diphenylpropylamines of type I (R = H) are devoid of pronounced analgesic activity in mice and rats. N : N ′-di iso propyl-3:3-diphenylpropylamine HCl shows antispasmodic and antinicotinic activity. Moreover, quaternization with methyl halides as a rule increases parasympatholytic activity and decreases all other activities of 3:3-diphenylpropylamines.