Water → N-(3-phenylpropan-1-yl)-N-[1-tert-butoxycarbonylpiperidin-4-ylmethyl]trifluoroacetamide

HRID 1978349Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[C:28]1([CH2:27][CH2:26][CH2:25][N:17]([CH2:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][CH2:12]2)[C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen, 0.25 g (6.25 mM) of a 60% suspension of sodium hydride in liquid paraffin was added to a solution of 1.73 g (5.57 mM) of N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)trifluoroacetoamide in N,N-dimethylformamide (20 ml) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. To this mixture was added 1.0 ml (6.58 mM) of 1-bromo-3-phenylpropane and the mixture was stirred at room temperature for 2.5 hours and further at 60° C. for one hour. The reaction was stopped by adding water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over MgSO4, and purified by column chromatography (ethyl acetate-hexane 30%) to provide the title compound.

Workup

stirringthe mixture was stirred at room temperature for 2.5 hours and further at 60° C. for one hour
extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried over MgSO4
custompurified by column chromatography (ethyl acetate-hexane 30%)

Sources & evidence

ORD record: ord-cf9322ae1a1a46739cfa3037d28cc2f0
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235731B1

Reaction notes

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