Chloroform → 3,4-Dichloro-N-(1-methyl-1-azaspiro[4.5]decan-4-yl)benzamide

Participants

Reaction Steps

To a stirring suspension of 3.0 g (0.017 mole) of 1-methyl-4-amino-azaspiro[4.5]decane of Example 2 and 5.0 g of NaHCO3 in 50 ml of CHCl3 was added dropwise 3.8 g (0.018 mole) of 2,4-dichlorobenzoyl chloride in 25 ml of CHCl3. The reaction was refluxed for 3 hours, cooled to room temperature, filtered, and the solvent evaporated to give an oil. The residue was triturated with boiling hexane and decanted; the hexane solution afforded 3.1 g of 1-methyl-4-(3,4-dichlorobenzamido)-1-azaspiro[4.5]decane on standing. The solid was dissolved in ether and a solution of ethereal HCl was added. The resulting solid was collected and recrystallized three times from ethanol to give 2.4 g (37.5%) m.p. 227°-229° C. of 1-methyl-4-(2,4-dichlorobenzamido)-1-azaspiro[4.5]decane hydrochloride.

Provenance & Evidence