2-(Dimethylamino)ethanol → HCID 59589521, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-dimethylethanolamine (0.23 ml, 2.3 mmol) in dry dimethylformamide (5 ml) was treated with sodium hydride (60% suspension in mineral oil, 0.092 g, 2.3 mmol) and heated at 50° C. for 30 minutes. The product from Step 2 (0.50 g, 2.1 mmol) was added and the reaction heated at 50° C. overnight. After cooling to room temperature the reaction mixture was applied to a SCX column and washed with methanol then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane solution (0.1:1.9:98 and 0.5:4.5:95) to afford the title compound (0.25 g, 48%); 1H NMR (CDCl3) 8.52 (2H, s), 4.45 (2H, t, J 8 Hz), 2.74 (2H, t, J 8 Hz), 2.33 (6H, s).

Provenance & Evidence