Ethanol → HCID 10095884, compound

HRID 370663Notes

Reaction equation

HRID 370663 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18]=3[O:27][CH3:28])=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[BH4-].[Na+].[Cl-].[NH4+]>O.C(Cl)(Cl)Cl>[C:29]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18]=3[O:27][CH3:28])[OH:16])[CH2:10][CH2:9]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10389536HCID 10389536, compound

Product 1

HCID 10095884HCID 10095884, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

13.8 g (30 mmol) of 2-(4-diphenylmethylpiperazinyl)-1-(2,3,4-trimethoxyphenyl)ethanone was dissolved in a mixed solvent consisting of 100 ml of ethanol and 30 ml of chloroform, followed by addition of 2.27 g (60 mmol) of sodium borohydride under ice-cooled conditions over 20 minutes. The resultant mixture was stirred at room temperature for 2 hours, followed by addition of 50 ml of an aqueous saturated solution of ammonium chloride and by further addition of 100 ml of water. The resultant mixture was extracted with 200 ml of ethyl acetate, and the organic layer was successively washed with water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was removed, and the residue was recrystallized from a mixed solvent of chloroform and ethanol to give 9.70 g of 2-(4-diphenylmethylpiperazinyl)-1-(2,3,4-trimethoxyphenyl)ethanol as white crystals (yield: 70%).

Workup

  1. temperaturecooled conditions over 20 minutes
  2. extractionThe resultant mixture was extracted with 200 ml of ethyl acetate
  3. washthe organic layer was successively washed with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-d4d7d27f601d422dac7eaef598e4e85d
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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