Triethylamine → HCID 57878582, compound

Participants

Reaction Conditions

Reaction Steps

3-Trifluoromethylphenylsulfonyl chloride (4) (12 g, 49 mmol, Aldrich) was added to a mixture of the crude compound 3, triethylamine (TEA, 10 mL) and dichloromethane (DCM, 10 mL) at room temperature. The resulting mixture was heated and stirred at 37° C. for 2 days. The reaction mixture was cooled to room temperature, washed with water (10 mL) and then with brine, and concentrated and purified by column (silica gel) eluting with EtOAc/hexanes (3/7) to afford 3-[N-cyclopropyl-N-(3-trifluoromethylbenzenesulfonyl)amino]piperidine-1-carboxylic acid tert-butyl ester (5) as a sticky oil (10 g, yield 45% in two steps), which was dissolved in 100 mL of 1,4-dioxane. HCl (10 mL, concentrated aq.) was added to the 1,4-dioxane solution at room temperature. The resulting mixture was stirred at room temperature for 48 hours, and concentrated under vacuum. The residue was washed with ethyl ether, and dried to obtain the desired title compound 6 as an oil (6.5 g, 81%). 1H NMR (400 MHz, CD3OD): δ 8.22 (d, j=7.9 Hz, 1H), 8.17 (s, 1H), 8.06 (d, j=7.8 Hz, 1H), 7.90 (d, 1H, j=7.8 Hz, 1H), 4.17-4.24 (m, 1H), 3.34-3.38 (m, 2H), 3.22-3.29 (m, 1H), 2.87-2.95 (m, 1H), 1.98-2.18 (m, 3H), 1.68-1.82 (m, 2H), 1.04-1.09 (m, 1H), 0.79-0.92 (m, 3H); LC: 100%; MS: m/z=349 (M+1).

Provenance & Evidence