HCID 58495622, compound → HCID 58495452, compound

HRID 1190998Notes

Reaction equation

HRID 1190998 reaction equation
[CH:1]1([C:7](=[O:17])[CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.Cl.[Pd]>[CH:1]1([C:7](=[O:17])[CH2:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 58495622HCID 58495622, compound

Product 1

HCID 58495452HCID 58495452, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen for 10 min into a solution of 4-(2-cyclohexyl-2-oxo-ethyl)-benzonitrile (478 mg, 2.10 mmol) in methanol (80 mL) with concentrated HCl (5 drops). Add 10% Pd/C (Degussa type E101, 96 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. Wash with diethyl ether/hexane (1:1) and filter the white solid. 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 (145 mg, 30%). MS (ES+) m/z: 232 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a0326ea3628c451299c0bbd810030568
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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