Triethylamine → 1-[(6-chloro-3-pyridinyl)sulfonyl]-N,N-dimethyl-4-Piperidinamine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	N,N-Dimethylpiperidin-4-amine	HCID 417391	—
Reactant	2-Chloro-5-pyridinesulfonyl chloride	HCID 2792792	—
Reactant	Dichloromethane methanol	HCID 21226129	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-[(6-chloro-3-pyridinyl)sulfonyl]-N,N-dimethyl-4-Piperidinamine	HCID 43430609	94.5%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a stirred ice-cooled solution of 4-(dimethylamino)piperidine (1.2 mL, 9.4 mmol), triethylamine (2.6 mL, 19 mmol), and 4-dimethylaminopyridine (0.012 g, 0.094 mmol) in DCM (18 mL) was added 6-chloropyridine-3-sulfonyl chloride (2.0 g, 9.4 mmol) in one portion. The resulting mixture was stirred at 0° C. for 1.5 h. Upon workup, the mixture was directly subjected to combi-flash column chromatography (methanol/DCM) to give compound 363 (2.7 g, 94% yield) as a white solid. LCMS-ESI (POS), M/Z, M+1: Found 304.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841312B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-f167625d6b5544b1b197359d6bc6ec00
Source note	uspto-grants-2014_09