HCID 59828906, compound → HCID 59828870, compound

HRID 1191054Notes

Reaction equation

HRID 1191054 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]([CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=[O:6]>CO.Cl.[Pd]>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]([CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)=[O:6]

Participants

5

Reactant 1

HCID 59828906HCID 59828906, compound

Product 1

HCID 59828870HCID 59828870, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of 4-[2-(2,2-dimethylpropyl-carbamoyl)-ethyl]-benzonitrile (740 mg, 3.0 mmol) in methanol (60 mL) with 3 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 148 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 (717 mg, 95%). 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-bf8558af012f440f8289d7dba93c5bdc
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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