1-Chloroethyl chloroformate → 5-(2-Chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride

To a solution of the 5-(2-chlorophenyl)-1,2,3,6-tetrahydro-1-methylpyridine (5.9 g) in dichloromethane (60 ml) was added 1-chloroethyl chloroformate (5.1 ml) and the mixture was stirred for 2.5 h. The mixture was washed with water and then with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give brown oil. A solution of the obtained oil in methanol was refluxed for 2 h. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate to give 5-(2-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (2.4 g). A solution of 5-(2-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (156 mg), 2-chloro-1,6-dihydro-1-methyl-6-oxo-4-(pyridin-4-yl)pyrimidine (150 mg) and triethylamine (236 μl) in dimethylformamide (3 ml) was stirred at room temperature for 6 h. To the reaction mixture was added water (3 ml), and the precipitated crystals were collected by filtration to give the title compound (240 mg) as white crystals.

1. washThe mixture was washed with water
2. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. customto give brown oil
5. customThe solvent was evaporated under reduced pressure
6. customthe obtained residue was crystallized from ethyl acetate

ORD record

ord-9e76839650c443358848b27bac5f2d6b

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683069B2