Sodium borohydride → HCID 3071160, compound

HRID 370660Notes

Reaction equation

HRID 370660 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:24]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[OH:16])[CH2:12][CH2:13]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 103401292-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone

Product 1

HCID 3071160HCID 3071160, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol was dissolved 3.0 g (7.8 mmol) of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone, to which 3.0 g (79 mmol) of sodium borohydride was added slowly under ice-cooled conditions. The reaction mixture was then stirred overnight at room temperature, and methanol was removed under reduced pressure. Thereafter, 100 ml of ether was added to the residue, and the solution was washed successively with water and saturated saline and dried over anhydrous sodium sulfate. The resultant ether solution was concentrated, and the residue was purified by silica gel column chromatography (silica gel 90 g; chloroform:methanol=100:1) to give 2.4 g of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanol (yield: 79%) which, upon recrystallization from a mixed solvent of ethyl acetate and n-hexane, gave white crystals.

Workup

  1. temperaturecooled conditions
  2. custommethanol was removed under reduced pressure
  3. additionThereafter, 100 ml of ether was added to the residue
  4. washthe solution was washed successively with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe resultant ether solution was concentrated
  7. customthe residue was purified by silica gel column chromatography (silica gel 90 g; chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-afb8743f98e245a082156e60b0db0e78
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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