Ethyl Acetate → HCID 10435214, compound

HRID 370662

Reaction equation

HRID 370662 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:42])[CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([OH:42])[CH2:22][N:23]2[CH2:24][CH2:25][N:26]([CH:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:27][CH2:28]2)=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 25517Ammonium ChlorideHCID 103227601-(4-Benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 10435214HCID 10435214, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 24 ml of tetrahydrofuran was suspended 0.60 g (16 mmol) of lithium aluminum hydride, to which a suspension consisting of 24 ml of tetrahydrofuran and 3.0 g (6.3 mmol) of 1-(4-benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanone was added portionwise under ice-cooled conditions. After being stirred for 0.5 hour, the resultant mixture was added dropwise with 5 ml of ethyl acetate, followed by further addition of 50 ml of ethyl acetate. The thus prepared solution was poured into an aqueous solution of ammonium chloride, and the organic layer was separated. The organic layer was washed twice with saturated saline and then dried over anhydrous sodium sulfate. The solvent was removed, and the residue was recrystallized from a mixed solvent of ethanol and chloroform to give 2.37 g of 1-(4-benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanol (yield: 79%).

Workup

  1. additionwas added portionwise under ice-
  2. temperaturecooled conditions
  3. customthe organic layer was separated
  4. washThe organic layer was washed twice with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was recrystallized from a mixed solvent of ethanol and chloroform

Sources & evidence

ORD record
ord-63c838f4feed4e71ab42cffecb96d306
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Linked notes

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