N-(2-((1-(4-chlorobenzyl)piperidin-4-yl)methylamino)-2-oxoethyl)-2-amino-5-(trifluoromethyl)benzamide → 4-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]aminomethyl]piperidine

HRID 2187834Notes

Reaction equation

ClC1C=CC(C[N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:31])[CH2:16][NH:17][C:18](=[O:30])[C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=3[NH2:29])[CH2:9][CH2:8]2)=CC=1>C(O)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:29][C:20]1[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:26])[F:27])=[CH:24][C:19]=1[C:18]([NH:17][CH2:16][C:15]([NH:14][CH2:13][CH:10]1[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1)=[O:31])=[O:30]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-(4-chlorobenzyl)-4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl]piperidine (447 mg, 0.93 mmol) and Pd(OH)2 (60 mg, 0.23 mmol) in 5% HCO2H/methanol (10 mL) was stirred at 50° C. for 14 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. To the residue was added 1 N aqueous NaOH solution (15 mL) and the mixture was extracted with ethyl acetate (30 mL×3). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=70/25/5) gave 4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl ]piperidine (284 mg, 86%): ESI/MS m/e 359.0 (M++H, Cl16H21F3N4O2).

Workup

filtrationThe Pd catalyst was filtered off through Celite
concentrationthe filtrate was concentrated
additionTo the residue was added 1 N aqueous NaOH solution (15 mL)
extractionthe mixture was extracted with ethyl acetate (30 mL×3)
dry with materialThe combined extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-cb3c39a201ba45c08bf1b6afec5fef98
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410566B1

Reaction notes

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