Dimethylformamide → HCID 58046633, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-1-(4-methylpiperazin-1-yl)ethanone in N,N-dimethylformamide (3 mL), was added tert-butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.2 g, 0.43 mmol) and potassium carbonate (0.119 g, 0.86 mmol). After stirring at 65° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and isolated by Biotage flash chromatography (2-20% methanol/dichloromethane) to obtain the title compound (0.16 g, 62%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.64 (t, 2H, J=12.8 Hz), 2.18 (s, 3H), 2.25-2.45 (m, 6H), 3.41-3.50 (m, 6H), 3.85 (br, 2H), 4.60-4.65 (m, 4H), 5.05 (s, 2H), 6.64-6.69 (m, 2H), 6.76-6.79 (m, 1H), 7.13-7.19 (m, 2H), 7.54-7.60 (m, 2H), 7.91-7.93 (m, 2H); MS for C33H43N5O6 m/z 606.08 (M+H)+.

Provenance & Evidence