Aniline → HCID 51204633, compound

Participants

Reaction Conditions

Reaction Steps

Part A: To a solution of N-Boc-isonipecotic acid (4.85 g, 21.2 mmol) in tetrahydrofuran (80 mL) at 25° C. was added carbonyl diimidazole (3.80 g, 23.3 mmol), and the reaction mixture was stirred for 1.00 h at 25° C. To the resulting mixture was added aniline (2.10 mL, 23.3 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) (3.20 mL, 21.2 mmol), and the solution was stirred at 25° C. for another 90 h. The reaction mixture was diluted with water, 1.00 N hydrochloric acid (80 mL), and ethyl acetate. The phases were separated, and the organic phase was washed with water (×2) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% diethyl ether/methylene chloride) furnished tert-butyl 4-(phenylcarbamoyl)-piperidine-1-carboxylate (4.25 g) as a white solid; 1H NMR (300 MHz, CDCl3) δ 7.48 (d, 2H, J=8.0 Hz), 7.29 (t, 2H, J=8.0 Hz), 7.20 (br s, 1H), 7.08 (t, 1H, J=8.0 Hz), 4.16 (m, 2H), 2.75 (m, 2H), 2.35 (m, 1H), 1.89-1.61 (m, 4H), 1.43 (s, 9H).

Provenance & Evidence