4-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzonitrile → 4-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzylamine

HRID 1191050Notes

Reaction equation

HRID 1191050 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=[O:7]>CO.Cl.[Pd]>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)=[O:7]

Participants

5

Reactant 1

HCID 584956644-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzonitrile

Product 1

HCID 584955314-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzylamineYield 107.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of 4-[(3,3-dimethylbutyl-carbamoyl)-methyl]-benzonitrile (240 mg, 0.9 mmol) in methanol (20 mL) with 3 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 48 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the catalyst over Celite® and concentrate the filtrate in vacuo. Elute the compound through a SCX column to obtain the title compound (240 mg, 98%). 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. washElute the compound through a SCX column

Sources & evidence

ORD record
ord-872a73bd2bc24f7db280d50b8e9966a5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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