Diisopropylethylamine → (2-Chloro-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-(4-(Trifluoromethyl)phenyl)piperazine	HCID 121718	—
Reactant	2-Chloro-5-(methylsulphonyl)benzoic acid	HCID 2329132	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(2-Chloro-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone	HCID 59793689	88.4%

Reaction Steps

To a solution of 2-Chloro-5-methanesulfonyl-benzoic acid (102 mg, 0.43 mmol) in dimethylformamide (20 ml) were successively added TBTU (153 mg, 0.48 mmol), N-ethyldiisopropylamine (0.28 ml, 2.17 mmol) and 1-(4-trifluromethylphenyl)piperazine (ABCR F07741NB, [30459-17-7], 100 mg, 0.43 mmol). The reaction was then stirred at room temperature for two hours, then concentrated in vacuo and purified by column chromatography (SiO2, 50 g, heptane/ethylacetate=0 to 100%), to give the title compound as a colorless gum (170 mg, 0.38 mmol). MS (m/e): 464.3 (M+NH4+, 100%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07427612B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-2fdd7b58dc9f441f95df9d9522d6456d
Source note	uspto-grants-2008_09