4-(1-Cyclohexen-1-yl)-3-(trifluoromethyl)benzamide → 4-Cyclohexyl-3-(trifluoromethyl)benzamide

HRID 423344Notes

Reaction equation

HRID 423344 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:17])([F:18])[F:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 592018284-(1-Cyclohexen-1-yl)-3-(trifluoromethyl)benzamide

Product 1

HCID 592017944-Cyclohexyl-3-(trifluoromethyl)benzamideYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(1-Cyclohexen-1-yl)-3-(trifluoromethyl)benzamide (D66) (850 mg, 3.16 mmol) was dissolved in methanol (63 ml) and hydrogenated using an H-Cube, using palladium on carbon at 40° C. with a flow rate of 2 mL/min. The solvent was removed in vacuo to give the title compound as a white solid (822 mg). δH (CDCl3, 400 MHz): 8.08 (1H, d), 7.94 (1H, dd), 7.52 (1H, d), 6.54 (2H, brs), 2.97 (1H, m), 1.90-1.75 (5H, m), 1.50-1.22 (5H, m). MS (ES): C14H16F3NO requires 271; found 272 (MH+).

Workup

  1. customat 40° C.
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-86a1e98d208a4a5ca43ce77942b69969
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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