Dimethylamine → 1-(4-ethynylphenyl)-N,N-dimethylmethanamine

Participants

Reaction Steps

Glacial acetic acid (3 drops) was added to a mixture of 4-ethynylbenzaldehyde (250.7 mg, 1.93 mmol), dimethylamine (2M in THF, 1.5 mL, 3.0 mmol) and NaBH(OAc)3 (617 mg, 2.91 mmol) in DCE (6.5 mL). The resulting mixture was stirred for 2.5 h at rt. The reaction was quenched with saturated aqueous NaHCO3 (˜40 mL). The product was extracted into CH2Cl2 (100 mL, then 2×50 mL), and the combined organic layer was washed with brine (25 mL), dried (Na2SO4) and evaporated in vacuo. Purification on Biotage Isolera (silica, 0-3% 2M NH3-methanol/CH2Cl2) gave 1-(4-ethynylphenyl)-N,N-dimethylmethanamine (280.1 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8 Hz, 2H), 7.28 (d, J=8 Hz, 2H), 3.42 (s, 2H), 3.07 (s, 1H), 2.24 (s, 6H).

Provenance & Evidence