Diethyl Ether → 1-[(3-Fluorophenyl)methyl]-4-(piperazin-1-yl)-1,3-dihydro-2H-indol-2-one

HRID 730574Notes

Reaction equation

HRID 730574 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][C:17](=[O:31])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCO.C(OCC)C>CCO>[F:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][N:18]1[C:19]2[C:15](=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:22]=[CH:21][CH:20]=2)[CH2:16][C:17]1=[O:31]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21887872Ethanol hydrochlorideHCID 57834987HCID 57834987, compound

Product 1

HCID 160422241-[(3-Fluorophenyl)methyl]-4-(piperazin-1-yl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[1-(3-Fluoro-benzyl)-2-oxo-2,3-dihydro-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (115 mg) was dissolved in 2 mL of EtOH and 500 uL of 2.0 N HCl/EtOH was added. The solution was heated to reflux on a steam bath for 30 minutes and then cooled to room temperature. Diethyl ether was added slowly to precipitate 1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one as a hydrochloride salt. MS: 326 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux on a steam bath for 30 minutes
  3. customto precipitate 1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one as a hydrochloride salt

Sources & evidence

ORD record
ord-8c97a340714945dd817478f454ec0747
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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