HCID 57656539, compound → HCID 57656471, compound

HRID 911754Notes

Reaction equation

HRID 911754 reaction equation
[CH3:1][C:2]([S:5]([CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)(=[O:7])=[O:6])([CH3:4])[CH3:3]>CO.Cl.[Pd]>[CH3:4][C:2]([S:5]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)(=[O:7])=[O:6])([CH3:1])[CH3:3]

Participants

5

Reactant 1

HCID 57656539HCID 57656539, compound

Product 1

HCID 57656471HCID 57656471, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 4-(2-methyl-propane-2-sulfonylmethyl)-benzonitrile (300 mg, 1.26 mmol) in methanol (50 mL). Add concentrated HCl (10 drops), 10% Pd/C (Degussa type E101, 60 mg) and submit the mixture to hydrogenation at atmospheric pressure for 1 h. Filter over Celite® and wash with methanol. Concentrate the filtrate in vacuo to give the hydrochloride salt of the title compound as a solid that was washed with diethyl ether (366 mg, 87%). Partition the solid between saturated NaHCO3 and EtOAc and extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give the title compound (195 mg, 74%). MS (ES+) m/z: 242 (M+H)+.

Workup

  1. customfor 1 h
  2. filtrationFilter over Celite®
  3. washwash with methanol
  4. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-96dd0500e29d4aafb282db142a037b02
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…