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

HRID 1790514Notes

Reaction equation

HRID 1790514 reaction equation
C(Cl)(=O)[O:2][CH2:3][CH3:4].F[CH2:8][C:9]([O-])=O.[Na+].[F:13][C:14]1[CH:38]=[CH:37][C:17]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][NH2:36])[CH:33]=4)[CH:28]=[CH:27]3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][N:36]5[CH2:9][CH2:8][CH2:4][C:3]5=[O:2])[CH:33]=4)[CH:28]=[CH:27]3)[CH2:24][CH2:25]2)=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 16212360Sodium FluoroacetateHCID 22038390HCID 22038390, compound

Product 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoleYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, ethyl chlorocarbonate (96 μl) was added to a suspension of sodium fluoroacetate (100 mg) in dimethylformamide (5 ml) and the resultant mixture was stirred for 20 min. Next, a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtainedinExample 322-3) indimethylformamide (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 (100 mg) as a white powder (yield: 57%).

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-1f6edfbacefb473bb7c0f45c91590ff7
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…