HCID 11676346, compound → HCID 11561090, compound

HRID 908980Notes

Reaction equation

HRID 908980 reaction equation
Cl.[CH3:2][N:3]([CH3:30])[C:4]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:9][CH2:8][C:7](=[CH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[CH2:6][CH2:5]1>[Pd].CO>[CH3:30][N:3]([CH3:2])[C:4]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:12])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 11676346HCID 11676346, compound2×

Product 1

HCID 11561090HCID 11561090, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 24 mg) was added to a solution of 2-[4-dimethylamino-4-(4-fluorophenyl)-cyclohexylidene]-N-(3-phenylpropyl)-acetamide (base of Example 19; 390 mg, 0.99 mmol) in abs. methanol (25 ml). The reaction mixture was hydrogenated at RT under a pressure of 2 bar for 17 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue (402 mg) by chromatography on silica gel (80 g) with EA/methanol (2:1), the less polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide was isolated as a beige-coloured oil in a yield of 24% (78 mg) and the more polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide was isolated as a colourless oily solid in a yield of 76% (297 mg).

Workup

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customAfter separation of the residue (402 mg) by chromatography on silica gel (80 g) with EA/methanol (2:1)

Sources & evidence

ORD record
ord-8f1061895d15463ab0686cbf61e0dadc
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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