HCID 58495692, compound → HCID 58495507, compound

HRID 1191041Notes

Reaction equation

HRID 1191041 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)=[O:4]>CO.Cl.[Pd]>[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][NH2:13])=[CH:14][CH:15]=1)=[O:4]

Participants

5

Reactant 1

HCID 58495692HCID 58495692, compound

Product 1

HCID 58495507HCID 58495507, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen for 15 min into a solution of 4-[2-(2,2-dimethyl-propionylamino)-ethyl]-benzonitrile (175 mg, 0.76 mmol) in methanol (31 mL) with concentrated HCl (3 drops). Add 10% Pd/C (Degussa type E101, 18 mg) and submit the mixture to hydrogenation at atmospheric pressure for 64 h. 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 (110 mg, 62%). MS (ES+) m/z: 235 (M+H)+.

Workup

  1. customfor 64 h
  2. filtrationFilter the catalyst through Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cb927348be8d466fae9fd2ec62eb0ccd
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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