Triethylamine → 2,4'-Bipyridin-3-yl(4-(3,4-difluorobenzyl)-4-hydroxypiperidin-1-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	[2,4'-Bipyridine]-3-carboxylic acid dihydrochloride	HCID 84819756	—
Reactant	4-(3,4-Difluorobenzyl)-4-hydroxypiperidine hydrochloride	HCID 86680863	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,4'-Bipyridin-3-yl(4-(3,4-difluorobenzyl)-4-hydroxypiperidin-1-yl)methanone	HCID 86680864	71.2%

Reaction Steps

A suspension of 2,4′-bipyridine-3-carboxylic acid dihydrochloride (0.30 g), 4-(3,4-difluorobenzyl)-4-hydroxypiperidine hydrochloride (0.38 g), HATU (0.63 g) and triethylamine (0.77 mL) in DMF (4.0 mL) was stirred at room temperature for 18 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (0.32 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193709B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-df0a62d1032a481cbe5ebc8d3fa36a8c
Source note	uspto-grants-2015_11