Реакция #166391

Уравнение реакции

6-chloropyridine-3-carbonyl chloride

tert-butyl 1-piperazinecarboxylate

triethylamine

methanol DCM

→

compound 351

Выход 89.0%

tert-Butyl 4-(2-chloronicotinoyl)piperazine-1-carboxylate

Выход 89.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Температураgradually warmed up to ambient temperature for 20 h

Методика

To a stirred ice-cooled solution of tert-butyl 1-piperazinecarboxylate (2.2 g, 12 mmol), triethylamine (3.2 mL, 23 mmol), and 4-dimethylaminopyridine (0.014 g, 0.11 mmol) in DCM (15 mL) was added 6-chloropyridine-3-carbonyl chloride (2.0 g, 11 mmol) in one portion. The resulting mixture was stirred at 0° C. and gradually warmed up to ambient temperature for 20 h. Upon workup, the mixture was subjected to combi-flash column chromatography (methanol/DCM) to give compound 351 (3.3 g, 89% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.46 (1 H, d, J=2.0 Hz), 7.74 (1 H, dd, J=8.2, 2.3 Hz), 7.42 (1 H, dd, J=8.2, 0.8 Hz), 3.20-4.02 (8 H, m), 1.48 (9 H, s). LCMS-ESI (POS), M/Z, M+1: Found 326.0.

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