HCID 55028620, compound → HCID 59828903, compound

HRID 1191037Notes

Reaction equation

HRID 1191037 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([NH:5][CH2:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:4]>CO.Cl.[Pd]>[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH2:12])=[CH:13][CH:14]=1)=[O:4]

Participants

5

Reactant 1

HCID 55028620HCID 55028620, compound

Product 1

HCID 59828903HCID 59828903, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen for 15 min into a solution of 4-[(2,2-dimethyl-propionylamino)-methyl]-benzonitrile (0.4 g, 1.85 mmol) in methanol (50 mL) with concentrated HCl (8 drops). Add 10% Pd/C (Degussa type E101, 40 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the catalyst through Celite® and concentrate in vacuo to obtain the hydrochloride salt of the title compound. Add saturated aqueous NaHCO3 and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound as a yellow oil (315 mg, 77%). MS (ES+) m/z: 221 (M+H)+.

Workup

  1. customat atmospheric pressure overnight
  2. filtrationFilter the catalyst through Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ee0a0aa1f1c248189e67ed5adc977e9b
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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