Acetic Acid → HCID 135482223, compound

Participants

Reaction Steps

A mixture of the aldehyde (6-3, 50 mg, 0.19 mmol), N-methylpiperazine (191 mg, 1.91 mmol), acetic acid (0.06 mL) and sodium triacetoxyborohydride (406 mg, 1.91 mmol) in N,N-dimethyl formamide (3 mL) was stirred at the ambient temperature for 11 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 30% methanol in ethyl acetate) afforded the desired product (6-4) as a light tan solid; 1H NMR (400 MHz, DMSO-d6) δ 13.34 (s, 1H), 11.56 (s, 1H), 8.23 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=8.4 Hz), 7.53 (s, 1H), 7.49 (t, 1H, J=7.6 Hz), 7.44 (d, 1H, J=8.4 Hz), 7.31 (t, 1H, J=7.6 Hz), 7.12–7.11 (m, 2H), 3.57 (s, 2H), 2.52–2.26 (m, 8H), 2.21 (s, 3H).

Provenance & Evidence