Pyridine → Hexahydro-1H-azepine-1-carbonyl chloride

Temperature

-10 °C

To a solution of azepane (2 g, 20.2 mmol) in 30 mL of anhydrous toluene was added DIEA (3.5 mL, 20.0 mmol) and pyridine (1.63 mL, 20.2 mmol). The mixture was cooled to −10° C. under nitrogen. Once at the prescribed temperature, carbon dioxide gas was bubbled through the solution for 30 min, and then a solution of thionyl chloride (1.74 mL, 24.0 mmol) in 10 mL of toluene was added at −10° C. Upon completion of addition, the reaction mixture was stirred for 1 hr while the temperature was kept under 10° C. The reaction mixture was then diluted with ethyl acetate, washed with cold 0.5 N HCl solution and brine, dried over Na2SO4, and concentrated to give the title compound (2.76 g, 85%) as a pale yellow oil.

1. customOnce at the prescribed temperature, carbon dioxide gas was bubbled through the solution for 30 min
2. additionUpon completion of addition
3. customwas kept under 10° C
4. washwashed with cold 0.5 N HCl solution and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-0da899de35e445908c6be2df228e4aa6

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579360B2