4-Fluoroaniline → N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

Participants

Reaction Steps

Following the procedure as described in step A of Preparation 2, making variations as required to replace 4-fluoroaniline with 4-fluorobenzylamine to react with dimethoxyacetaldehyde followed by the imine reduction with sodium triacetoxyborohydride, N-(4-fluorobenzyl)-2,2-dimethoxyethanamine was obtained in 71% yield: 1H NMR (300 MHz, CDCl3) δ 7.24-7.19 (m, 2H), 6.97-6.89 (m, 2H), 4.43-4.39 (m, 1H), 3.70 (s, 2H), 3.30 (s, 6H), 2.67 (dd, J=5.4, 1.5 Hz, 2H); MS (ES+) m/z 214.3 (M+1).

Provenance & Evidence