Diethyl Ether → HCID 22462243, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Pyridyl)piperidine (2.44 g) was added to a stirred suspension of 1-t-butoxycarbonyl-4-(4-nitrophenoxycarbonyl)piperazine (5.26 g) in dimethylformamide (90 mL) at 25° C. The reaction mixture was heated at 105° C. for 18 hours. The dimethylformamide was evaporated and water (500 mL) added, The aqueous phase was extracted with ethyl acetate. The organic phase was washed with 1M sodium hydroxide solution (5×100 mL) and saturated brine (2×100 mL), dried and evaporated, The residue was purified by chromatography on silica gel using a mixture of dichloromethane: methanol: 0.88 ammonia (94:5:1) as eluent to give a yellow oil. Trituration with ether gave, as a pale yellow solid, 1-t-butoxycarbonyl-4-[4-(4-pyridyl)-1-piperidylcarbonyl]piperazine (2.62 g); mp 143-4° C.; NMR (CDCl3) 1.44(s, 9H), 1.58-1.78(m, 2H), 1.78-1.92(d, 2H), 2.60-2.75(m, 1H), 2.80-2.96 (m, 2H), 3.92-3.25(t, 4H), 3.38-3.50(m, 4H), 3.82(d, 2H), 7.10(d, 2H), 8.51(d, 2H); EI-MS m/z 375(M+H).

Provenance & Evidence