1-(3-(Trifluoromethyl)phenyl)piperazine → [(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Participants

Role	Name	HCID	Charge
Reactant	1-(3-(Trifluoromethyl)phenyl)piperazine	HCID 4296	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid	HCID 86625301	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Triethylamine	HCID 8471	—
Product	[(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone	HCID 86625302	10.6%

Reaction Steps

The mixture of 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid (65 mg, 0.146 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (54.5.0 mg, 0.292 mmol), N-hydroxybenzotriazole (20.7 mg, 0.146 mmol), and 1-(3-trifluoromethyl-phenyl)-piperazine (29.67 mg, 0.219 mmol), triethylamine (0.08 ml) in dry dichloromethane (2 mL) was stirred overnight, and then concentrated. The residue was purified by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient to afford the title compound (10.2 mg, 10.6%) as a light yellow oil. MS m/e=659.4 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07528136B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-20fa11b5f5c245a69a21324fefbe55a4
Source note	uspto-grants-2009_05