Ethanol → HCID 57656193, compound

HRID 911622Notes

Reaction equation

HRID 911622 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])=[C:5]([F:19])[CH:4]=1)#[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])=[C:5]([F:19])[CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 57656527HCID 57656527, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57656193HCID 57656193, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Add 4-cyano-N-cycloheptyl-2-fluoro-benzamide (1.4 g, 5.4 mmol), 10% Pd/C (Degussa type E101, 415 mg), ethanol (40 mL), water (15 mL) and acetic acid (1.8 mL) to a pressure vessel. Pressurize the vessel to 55 psi with hydrogen, and stir the mixture for 0.5 h (monitor the reaction by TLC). 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 product as the acetic acid salt. Use SCX chromatography to obtain the title compound (1.36 g, 95%). GC-MS m/z: 264 (M+).

Workup

  1. customthe reaction by TLC)
  2. filtrationFilter the mixture through Celite®
  3. washwash the cake with warm ethanol
  4. concentrationConcentrate the filtrate in vacuo
  5. customto obtain the product as the acetic acid salt

Sources & evidence

ORD record
ord-a276c42899a342f3bfce349c369feb9b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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