Hydrochloric Acid → N-methyl-N-nitrosobenzeneethanamine

Participants

Reaction Conditions

Reaction Steps

A sample of N-methyl-2-phenylethylamine hydrochloride (6.4 g, 37.3 mmol) was dissolved in water (18 ml), ethanol (11 ml) and 2N hydrochloric acid (4 ml) were introduced and the solution was heated to 70° C. A solution of sodium nitrite (2.6 g, 37.7 mmol) in water (11 ml) was added dropwise to the reaction mixture over 30 min. During the addition the reaction mixture was acidified with 2N hydrochloric acid (4 ml). Cooling was followed by extraction with n-heptane (4×100 ml); the combined extracts were dried (MgSO4) and evaporated in vacuo to provide the N-methyl-N-nitroso-2-phenylethylamine as an oil (5.0 g, 81%) (a ca. 65:35 mixture of apparent geometric isomers), 1H NMR (DMSO-d6) γ 2.98 (3H, s,--CH3), 3.05 (2H, t, PhCH2 --), 4.37 (2H, t, --CH2 --N--), 7.13-7.36 (5 H, m, Ar-H) (major isomer); 2.78 (2H, t, PhCH2 --), 2.98 (3H, s,--CH3), 3.77 (2H, t,--CH2 --N--), 7.13-7.36 (5H, m, Ar-H) (minor isomer).

Provenance & Evidence