Ethanol → HCID 57655973, compound

HRID 911623Notes

Reaction equation

HRID 911623 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][C:4]=1[F:19])#[N:2].C(O)C.O.[H][H]>[Pd].C(O)(=O)C>[NH2:2][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][C:4]=1[F:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 57656528HCID 57656528, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57655973HCID 57655973, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Add 4-cyano-N-cycloheptyl-3-fluoro-benzamide (0.86 g, 3.3 mmol), 10% Pd/C (Degussa type E101, 250 mg), ethanol (25 mL), water (9 mL) and acetic acid (1 mL) to a pressure vessel under a nitrogen atmosphere. Pressurize the vessel to 50 psi with hydrogen, and stir the mixture for 0.5 h. Filter the mixture through Celite® and wash the cake with warm ethanol followed by dichloromethane under a nitrogen atmosphere. Concentrate the filtrate in vacuo to obtain the title compound as the acetic acid salt. Use SCX chromatography to obtain the title compound (805 mg, 92%). MS (ES+) m/z: 265.3 (M+H)+.

Workup

  1. filtrationFilter the mixture through Celite®
  2. washwash the cake with warm ethanol
  3. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-08aa38e88b2548b682ca9d7bcbc90711
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…