Water → HCID 22393594, compound

HRID 1071642Notes

Reaction equation

HRID 1071642 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][CH2:16][C:17]2([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]2([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22393705HCID 22393705, compound

Product 1

HCID 22393594HCID 22393594, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-4-[3-[1-(4-fluorophenyl)cyclohexyl]-1-oxopropyl]piperazine (5.90 g) was dissolved in tetrahydrofuran (100 ml), and 80% lithium aluminum hydride, (1.03 g) was added thereto under ice-cooling. After heating under reflux for 1.5 hours, the mixture was cooled as it was to room temperature. Under ice-cooling, water, a 1N aqueous sodium hydroxide and further water were added thereto, and the insoluble matters were filtered off. The filtrate was evaporated, and the resulting residue was recrystallized from ethanol, to give 4.48 g (79%) of the title compound as white crystals.

Workup

  1. temperatureunder ice-cooling
  2. temperatureAfter heating
  3. temperatureunder reflux for 1.5 hours
  4. temperaturethe mixture was cooled as it
  5. customwas to room temperature
  6. temperatureUnder ice-cooling
  7. filtrationthe insoluble matters were filtered off
  8. customThe filtrate was evaporated
  9. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e0c292bdb9c7421ba2e26e8ba7d6e9a7
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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