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

HRID 1259357Notes

Reaction equation

[F:1][CH:2]([F:5])[CH2:3]Br.[Cl:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=1.C(N(CC)CC)C>CN1CCCC1=O>[Cl:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][CH2:3][CH:2]([F:5])[F:1])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

19.9 g (0.135 mol) of 2,2-difluoro-1-bromoethane, 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. The mixture is heated to 100° C. for 2 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 50 ml of water. 2 ml of 45% sodium hydroxide solution are used to adjust the pH to 12, and the mixture is then extracted twice with 30 ml of toluene. The product is subsequently finely distilled under reduced pressure. This gives 11.5 g of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine (corresponds to 83.1% yield).

Workup

temperaturecooled again to 80° C
distillationThe N-methylpyrrolidone is distilled off at 80° C. under reduced pressure
additionthe reaction mixture is poured onto 50 ml of water
extractionthe mixture is then extracted twice with 30 ml of toluene
distillationThe product is subsequently finely distilled under reduced pressure

Sources & evidence

ORD record: ord-6b04cbf4c7aa41deb0ae78c5c8080229
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466293B2

Reaction notes

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