Acetyl chloride → HCID 86677953, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round-bottomed flask, [(R)-1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-carbamic acid tert-butyl ester (1.20 g, 4.25 mmol) was combined with MeOH (100 ml) to give a colorless suspension. The reaction mixture was place under a nitrogen atmosphere and cooled in an ice bath. Acetyl chloride (6.04 ml, 85.0 mmol) was added slowly. The reaction mixture was stirred at 5° C. for an additional 10 min then warmed to room temperature. After stirring at room temperature for 17 h, the reaction mixture was concentrated to dryness to afford 1.10 g (quantitative) of (R)-1-(2,2,2-trifluoroethyl)piperidin-3-amine dihydrochloride as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ: 8.27 (br. s., 3H), 3.39 (q, J=10.2 Hz, 2H), 3.15-3.27 (m, 1H), 3.10 (dd, J=11.3, 3.0 Hz, 1H), 2.83 (app d, J=11.7 Hz, 1H), 2.56 (d, J=10.2 Hz, 1H), 2.45 (d, J=9.8 Hz, 1H), 1.83-2.04 (m, 1H), 1.62-1.83 (m, 1H), 1.45-1.62 (m, 1H), 1.25-1.45 (m, 1H).

Provenance & Evidence