Triethylamine → (2-Methylbenzenesulfonyl)-carbamic Acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	o-Toluenesulfonyl Isocyanate	HCID 2733313	—
Reactant	2-[4-Chloro-2-(hydroxymethyl)phenoxy]-1-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl}ethan-1-one	HCID 54563462	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Toluene	HCID 1140	—
Product	(2-Methylbenzenesulfonyl)-carbamic Acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl Ester	HCID 69655479	—

Reaction Conditions

Temperature	55 °C

Reaction Steps

To a solution of 2-(4-chloro-2-hydroxymethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.050 g, 0.12 mmol) in dry toluene (2 mL) was added triethylamine (0.05 mL, 0.36 mmol) followed by o-toluenesulfonylisocyanate (0.05 mL, 0.36 mmol) and catalytic 4-dimethylaminopyridine. After 23 hours the reaction was warmed to 55° C. for 2 hours. After cooling the reaction was evaporated to dryness and the title compound purified by silica gel chromatography (0.074 g, LRMS: 618.1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07098212B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-3c0eb05c8a254cc7ada9c39c6c9c73e0
Source note	uspto-grants-2006_08