Hydrazine → tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (120 g, 520 mmol) in DCM (250 mL) was added carbonyldiimidazole (96 g, 590 mmol) in portions at room temperature. After 30 minutes, the reaction mixture was added to a freshly prepared solution of hydrazine (27 g, 840 mmol) in DCM (100 mL). After 30 minutes, the reaction was washed with a saturated solution of sodium carbonate, brine, dried over sodium sulfate, filtered and concentrated. The resulting solid was suspended in ether and filtered to give tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 4.15-4.10 (s, 2H), 3.95-3.90 (m, 2H), 2.80-2.60 (m, 2H), 2.25-2.20 (m, 1H), 1.62-1.55 (m, 2H), 1.40 (s, 9H).

Provenance & Evidence