알킬할라이드와 Triethylamine을 이용한 일급 아로미틱 아민의 N-알킬레이션

N-Alkylation of Primary Aromatic Amines Using Alkylhalide and Triethylamine

Synthetic method for the selective N-monoalkylation of anilines using alkyl halides and triethylamine under room temperature was described. The corresponding N-alkylanilines were obtained in good yields with minor quantities of dialkylated products. Anilines 2a-m and 3a-m were identified using NMR and IR. A series of 2a-m and 3a-m has been synthesized from aniline, toluidines, ethylanilines, aminoacetophenones, phenetidines. Formation of anilines was undertaken with dropping of alkylhalides at room temperature in methanol (or ethanol) for 3 hours~5 days. Selectivity on the monoalkylation was relatively high. Synthetic ratio of monoalkylated and dialkylated product was 94 : 6 in case of maximum monoalkylation.