1-Iodopropane → Tert-butyl 4-[(6-chloropyrazin-2-yl)(propyl)amino]piperidine-1-carboxylate

To a stirred solution of tert-butyl 4-[(6-chloropyrazin-2-yl)amino]piperidine-1-carboxylate (0.20 g, 0.64 mmol) in tetrahydrofuran (3 mL) at 0° C. was added 1-iodopropane (1 mL, 10 mmol) and sodium hyrdride (0.051 g, 1.3 mmol). The reaction mixture was warmed to room temperature then stirred at 60° C. After 1.5 h, the reaction mixture was cooled to room temperature and quenched with water (10 mL). The reaction mixture was extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine (10 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford tert-butyl 4-[(6-chloropyrazin-2-yl)(propyl)amino]piperidine-1-carboxylate as a yellow oil. LRMS (ESI) calculated for C17H27ClN4O2 [M+Na]+, 377.2; found 377.1.

1. temperaturethe reaction mixture was cooled to room temperature
2. customquenched with water (10 mL)
3. extractionThe reaction mixture was extracted with EtOAc (3×25 mL)
4. washThe combined organic layers were washed with brine (10 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient)

ORD record

ord-d656a28c4649461491ea615adc249425

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183245B2