Acetate → HCID 20534880, compound

Participants

Reaction Conditions

Reaction Steps

To a cold stirred solution of 2.0 g. of N-n-hexyl-4-(4-nitrophenyl)butylamine in 7 ml. of formic acid were added dropwise 7 ml. of 37% aqueous formaldehyde. The reaction mixture was heated to 95° C. and stirred at this temperature for sixteen hours.The reaction mixture next was cooled and acidified by the addition of 10 ml. of 4 N hydrochloric acid. The aqueous acid mixture was washed twice with diethyl ether, and then made alkaline by the addition of 5 N sodium hydroxide. The product was extracted into diethyl ether. The ethereal extracts were combined, washed with water and dried. Removal of the solvent by evaporation under reduced pressure provided 2.2 g. of N-methyl-N-n-hexyl-4-(4-nitrophenyl)butylamine. The amine was dissolved inethyl acetate and treated with oxalic acid to give, after crystallization from isopropanol, 2.1 g. of N-methyl-N-n-hexyl-4-(4-nitrophenyl)butylaminium oxalate. M.P. 103°-105° C.

Provenance & Evidence