Ethanol → HCID 57656109, compound

HRID 911626Notes

Reaction equation

HRID 911626 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]([CH3:19])[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]([CH3:19])[CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 57656042HCID 57656042, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57656109HCID 57656109, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Add 4-cyano-N-cycloheptyl-2-methyl-benzamide (0.82 g, 3.2 mmol), ethanol (23 mL), water (8 mL) and acetic acid (1 mL) to a pressure vessel. Heat vessel to 50° C. to dissolve all solids. Add 10% Pd/C (Degussa type E101, 250 mg) under a nitrogen atmosphere, then pressurize the vessel to 55 psi with hydrogen at ambient temperature. Stir the mixture for 40 min. Filter the mixture through Celite® and wash the cake with warm ethanol (50 mL) followed by dichloromethane (100 mL) 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 (820 mg, 98%). MS (ES+) m/z: 261.3 (M+H)+.

Workup

  1. dissolutionto dissolve all solids
  2. customat ambient temperature
  3. filtrationFilter the mixture through Celite®
  4. washwash the cake with warm ethanol (50 mL)
  5. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-9c7e2e97711c4cc6bd88e1d5d3284249
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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