Triethylamine → 1-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine

Participants

Reaction Conditions

Reaction Steps

Triethylamine (5 mL) was added to a solution of 3-methoxy-4-nitrobenzyl alcohol (2.5 g, 13.6 mmol) in 50 mL of methylene chloride, and the mixture was cooled to 0° C. under nitrogen. Methanesulfonyl chloride (1.9 g, 16.3 mmol) was added dropwise and the mixture stirred at this temperature for 1 hour. Triethylamine (5 mL) was added, followed by dimethylamine hydrochloride (1.6 g, 20.4 mmol). After 5 minutes, the cooling bath was removed, and the mixture stirred at ambient temperature for 2.5 hours. The mixture was diluted with methylene chloride (75 mL) and washed with water (3×75 mL), and extracted into dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with methylene chloride (3×75 mL), basified (3N NaOH), and extracted into methylene chloride (3×75 mL). The combined organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 1.8 g of the product, in 65% yield: 1H NMR (CDCl3) δ 2.26 (s, 6H), 3.45 (s, 2H), 3.97 (s, 3H), 6.95 (d, J=8.2 Hz, 1H), 7.12 (s, 1H), 7.82 (d, J=8.2 Hz, 1H).

Provenance & Evidence