Triethylamine → 4-(1-((2-Chloropyridin-3-yl)carbonyl)-4-hydroxypiperidin-4-yl)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Chloronicotinic acid	HCID 76258	—
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	4-(4-Cyanobenzyl)-4-hydroxypiperidine hydrochloride	HCID 86680846	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(1-((2-Chloropyridin-3-yl)carbonyl)-4-hydroxypiperidin-4-yl)benzonitrile	HCID 86680860	104%

Reaction Steps

A suspension of 2-chloronicotinic acid (0.20 g), 4-(4-cyanobenzyl)-4-hydroxypiperidine hydrochloride (0.32 g), HATU (0.72 g) and triethylamine (0.89 mL) in DMF (4.0 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and filtered through basic silica gel. The filtrate was concentrated under reduced pressure to give the title compound (0.45 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440990B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-0a27b93eed6d40d1858e2eaa50c774b8
Source note	uspto-grants-2016_09