Ethyl Acetate → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole

HRID 1790513Notes

Reaction equation

HRID 1790513 reaction equation
F[CH:2](F)[C:3]([OH:5])=O.[F:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][NH2:30])[CH:27]=4)[CH:22]=[CH:21]3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+].[C:38](OCC)(=O)[CH3:39]>CN(C)C=O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][N:30]5[CH2:39][CH2:38][CH2:2][C:3]5=[O:5])[CH:27]=4)[CH:22]=[CH:21]3)[CH2:18][CH2:19]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9788Difluoroacetic acidHCID 516892Sodium BicarbonateHCID 22038390HCID 22038390, compound

Product 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoleYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under ice cooling, N,N′-carbonyldiimidazole (160 mg) was added to a solution of difluoroacetic acid (96 mg) in dimethylformamide (5 ml) and the resultant mixture was stirred for 30 min. Next, a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3) in dimethylformamide (5 ml) was added thereto and the resultant mixture was stirred at room temperature for 2 hr. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixtures. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (120 mg) as a white powder (yield: 65%).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-5878ea9430eb41c6b46a4d9002ff9adc
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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