Methanol → 1-(4-chlorobenzyl)-4-[[N-(3,5-bis(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

A solution of 3,5-bis(trifluoromethyl)benzoyl chloride (0.058 mmol) in dichloromethane (1 mL) was added to a mixture of 1-{4-chlorobenzyl)-4-((glycylamino)methyl}piperidine (0.050 mmol) and piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 mL). After the reaction mixture was stirred at room temperature for 2 h, methanol (1.0 mL) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was loaded onto Varian™ SCX column, and washed with CH3OH (16 mL). Product was eluted off using 2 N NH3, in CH3OH (6 mL) and concentrated to afford 1-(4-chlorobenzyl)-4-[{N-(3,5-bis(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (Compound No. 1213) (24.0 mg, 90%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 536.2 (M++H, C24H24ClF6N3O2).

1. stirringthe mixture was stirred at room temperature for 30 min
2. washwashed with CH3OH (16 mL)
3. washProduct was eluted off
4. concentrationin CH3OH (6 mL) and concentrated

ORD record

ord-269902fa29484300a9c374fc4b7af816

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362177B1