Dimethylamine, hydrochloride → HCID 21048997, compound

Participants

Reaction Steps

To a stirred solution of the product from Example 185 (74 mg, 0.14 mmol.) in methanol (5 ml) was added dimethylamine hydrochloride (58 mg, 0.7 mmol.). The mixture was stirred 5 minutes, sodium cyanoborohydride (27 mg, 0.42 mmol.) and sodium acetate (34 mg, 0.4 mmol.) added, and the mixture stirred a further 18 hours at ambient temperature. Ethyl acetate (20 ml) was added and the mixture washed with 1N sodium hydroxide and brine, dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate to afford the desired product (21 mg). 1H NMR (CDCl3) δ 7.37 (2H, d, J=8.6 Hz), 7.32 (2H, d, J=8.6 Hz), 7.09–7.04 (2H, m), 6.88–6.81 (1H, m), 4.49 (1H, d, J=6.4 Hz), 3.87–3.78 (4H, m), 3.59 (1H, m), 3.08 (1H, m), 2.6–2.5 (2H, m), 2.41–2.33 (2H, m), 2.17 (6H, s), 2.05–2.00 (2H, m) and 1.53–1.41 (2H, m). MS (ES+) 548 ([MH]+).

Provenance & Evidence