p-Toluenesulfonic acid → HCID 20534900, compound

Participants

Reaction Steps

Isopentylamine was reacted with 4-(4-nitrophenyl)butyanoyl chloride to provide N-isopentyl-4-(4-nitrophenyl)butyramide, which when reduced by reaction with diborane afforded N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of the latter compound with acetyl chloride under the conditions of Example 22 gave N-acetyl-N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of 21.8 g. of N-acetyl-N-isopentyl-4-(4-nitrophenyl)butylamine with 220 ml. of 1 M diborane in tetrahydrofuran provided, after workup according to the method of Example 22, 19.8 g. of N-ethyl-N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of the amine with para-toluenesulfonic acid in ethyl acetate afforded N-ethyl-N-isopentyl-4-(4-nitrophenyl)butylaminium tosylate. M.P. 78°-80° C.

Provenance & Evidence