Triethylamine → N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

Temperature

120 °C

13.7 g (0.135 mol) of 2,2-difluoro-1-chloroethane, 10 g (0.067 mol) of 1-(6-chloropyridin-3-yl)methanamine and 8.2 g of triethylamine are initially charged with 31 g of N-methylpyrrolidone. In addition, 4 g (0.033 mol) of potassium bromide are added. The mixture is heated to 120° C. under autogenous pressure in an autoclave for 16 hours and then cooled again to 80° C. The N-methylpyrrolidone is distilled off at 80° C. under reduced pressure and the reaction mixture is poured onto 20 ml of 32% hydrochloric acid. The mixture is concentrated to dryness under reduced pressure and then adjusted to pH 12 with 10 ml of 45% NaOH. The mixture is extracted three times with 30 ml of toluene and the organic phases are distilled under reduced pressure. This gives 9.8 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine (corresponds to 71% yield).

1. temperaturecooled again to 80° C
2. distillationThe N-methylpyrrolidone is distilled off at 80° C. under reduced pressure
3. additionthe reaction mixture is poured onto 20 ml of 32% hydrochloric acid
4. concentrationThe mixture is concentrated to dryness under reduced pressure
5. extractionThe mixture is extracted three times with 30 ml of toluene
6. distillationthe organic phases are distilled under reduced pressure

ORD record

ord-ec5e547f6ed74ce798eee751c43d719e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466293B2