Bromoacetonitrile → N-((1-(cyanomethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 1046548Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH2:3][CH2:2]1.[CH3:25][CH2:26][N:27](C(C)C)C(C)C.BrCC#N>CC#N>[C:26]([CH2:25][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=2)[CH2:3][CH2:2]1)#[N:27]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(piperidin-4-ylmethyl)-3,5-bis(trifluoromethyl)benzamide (3.54 g, 10.0 mmol) was dissolved in CH3CN (100 mL). DIPEA (1.94 g, 15.0 mmol) and bromoacetonitrile (1.32 g, 11.0 mmol) were added. The reaction mixture was heated at 50° C. overnight. The solvent was removed in vacuo. Saturated NaHCO3 (40 mL) was added and the mixture was extracted with CH2Cl2 (4×30 mL). The combined organic solution was dried over anhydrous Na2SO4 and passed through a silica gel plug. The desired compound was eluted off with EtOAc. The product was further purified by crystallization from EtOAc/petroleum ether as a white solid (3.62 g, 92%).

Workup

customThe solvent was removed in vacuo
additionSaturated NaHCO3 (40 mL) was added
extractionthe mixture was extracted with CH2Cl2 (4×30 mL)
dry with materialThe combined organic solution was dried over anhydrous Na2SO4
washThe desired compound was eluted off with EtOAc
customThe product was further purified by crystallization from EtOAc/petroleum ether as a white solid (3.62 g, 92%)

Sources & evidence

ORD record: ord-0203ba48e9c64d0bba9466732afb5cc3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569344B2

Reaction notes

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