(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile → (+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzylamine

HRID 1191048Notes

Reaction equation

HRID 1191048 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]([CH:7]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[CH3:8])=[O:6]>CO.Cl.[Pd]>[CH3:17][C:2]([CH3:1])([CH3:18])[CH2:3][NH:4][C:5]([CH:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)[CH3:8])=[O:6]

Participants

5

Reactant 1

HCID 58495675(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile

Product 1

HCID 58495650(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzylamineYield 85%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of (±)-4-[1-(2,2-dimethylpropyl-carbamoyl)-ethyl]-benzonitrile (80 mg, 0.33 mmol) in methanol (9 mL) with 2 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 8 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the catalyst over Celite® and concentrate the filtrate in vacuo. Partition the solid between saturated aqueous NaHCO3 and EtOAc, and extract again with EtOAc. Dry the combined organics extracts over MgSO4, filter and concentrate in vacuo to afford the title compound as a yellow oil (69 mg, 85%). MS (ES+) m/z: 249 (M+H)+.

Workup

  1. customat atmospheric pressure overnight
  2. filtrationFilter the catalyst over Celite®
  3. concentrationconcentrate the filtrate in vacuo
  4. customPartition the solid between saturated aqueous NaHCO3 and EtOAc
  5. extractionextract again with EtOAc
  6. customDry the combined
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b30a9b89adb144a785d56c86483119f4
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…