6-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin → 6-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylmethyl}-1,4-benzodioxin

HRID 37182

Reaction equation

HRID 37182 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[CH:40]=[CH:39][C:11]2[O:12][C:13]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH:24]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)=O)=[CH:14][O:15][C:10]=2[CH:9]=1>C(OCC)C>[OH:7][C:8]1[CH:40]=[CH:39][C:11]2[O:12][C:13]([CH2:16][N:18]3[CH2:19][CH2:20][N:21]([CH:24]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[CH2:22][CH2:23]3)=[CH:14][O:15][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 98044716-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxinHCID 21226445Aluminium lithium hydride

Product 1

HCID 104338936-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylmethyl}-1,4-benzodioxinYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, heat at reflux for 3 hours, in the presence of 5 mmol of lithium aluminium hydride, a solution of 2 mmol of 6-hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin in 35 cm3 of diethyl ether. After cooling, hydrolysis, removal of the insoluble mineral compounds by filtration and drying over magnesium sulfate, the compound obtained is purified by chromatography on a column of silica (eluant:petroleum ether/ethyl acetate, 40:60). 6-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin -1-ylmethyl}-1,4-benzodioxin is thereby obtained in a yield of 85%.

Workup

  1. temperatureUnder a nitrogen atmosphere, heat
  2. temperatureAfter cooling
  3. customhydrolysis, removal of the insoluble mineral compounds
  4. filtrationby filtration
  5. dry with materialdrying over magnesium sulfate
  6. customthe compound obtained
  7. customis purified by chromatography on a column of silica (eluant:petroleum ether/ethyl acetate, 40:60)

Sources & evidence

ORD record
ord-338a79a26a044e9f9f1fbe3ecf1e1c35
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Linked notes

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