Water → HCID 21563327, compound

HRID 1580627Notes

Reaction equation

HRID 1580627 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH3:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH2:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28][CH2:27]1)=O)=[CH:19][C:18]([F:38])=[CH:17][CH:16]=2.O>O1CCCC1>[CH3:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][N:26]1[CH2:31][CH2:30][N:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:28][CH2:27]1)=[CH:19][C:18]([F:38])=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 21563356HCID 21563356, compound

Product 1

HCID 21563327HCID 21563327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 21 g of lithium aluminum hydride and 100 ml of dry ether was added dropwise a solution of 67.5 g of 1-[β-(2-methyl-5-fluoro-3-indolyl)propionyl]-4-phenylpiperazine in 900 ml of tetrahydrofuran over a period of 90 minutes under gentle refluxing. Stirring and refluxing were continued for additional 4 hours and to the reaction mixture was added dropwise a mixture of water and tetrahydrofuran under cooling with ice. The resulting precipitate was filtered off and the filtrate was evaporated to dryness. Recrystallization of the residue from benzene gave 2-methyl-3-[γ-(4-phenylpiperazino)propyl]-5-fluoroindole having a melting point of 146.0°-147.0°C.

Workup

  1. temperaturerefluxing
  2. additionwas added dropwise
  3. temperatureunder cooling with ice
  4. filtrationThe resulting precipitate was filtered off
  5. customthe filtrate was evaporated to dryness
  6. customRecrystallization of the residue from benzene

Sources & evidence

ORD record
ord-3e6d534715a543e299a25e76c8e2e29f
Source dataset
uspto-grants-1976_01
Patent number
US03933824

Reaction notes

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