Ether hydrochloride → 4-[{N-(3(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine

HRID 279312Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[F:29][C:26]([F:27])([F:28])[C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][CH2:17][C:16]([NH:15][CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:31])=[O:30]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-(tert-butoxycarbonyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (2.29 g, 5.16 mmol) in CH3OH (40 mL) was treated with 1 N HCl-Et2O (55 mL). The reaction mixture was stirred at 25° C. for 15 h and the solvent was removed under reduced pressure. 2 N aqueous NaOH solution (100 mL) was added to the reaction mixture and the mixture was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine and dried (K2CO3). The solvent was removed under reduced pressure to afford a white solid which was purified by column chromatography (SiO2, CH3OH/CH2Cl2/Et3N=7/6/1)) to give 4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine as a white solid (1.27 g, 72%): The purity was determined by RPLC/MS (98%); ESI/MS m/e 344.1 (M++H, C16H20F3N3O2).

Workup

customthe solvent was removed under reduced pressure
addition2 N aqueous NaOH solution (100 mL) was added to the reaction mixture
extractionthe mixture was extracted with EtOAc (3×100 mL)
washThe combined extracts were washed with brine
dry with materialdried (K2CO3)
customThe solvent was removed under reduced pressure
customto afford a white solid which
customwas purified by column chromatography (SiO2, CH3OH/CH2Cl2/Et3N=7/6/1))

Sources & evidence

ORD record: ord-a8b2e11a92cf4123a135cb71336a01a9
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362177B1

Reaction notes

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