Acetone → 3-(4-Isopropyl-piperazin-1-yl)-phenol

HRID 910274Notes

Reaction equation

HRID 910274 reaction equation
[CH3:1][C:2]([CH3:4])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[N:19]1([C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:2]([N:22]1[CH2:21][CH2:20][N:19]([C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23]1)([CH3:4])[CH3:1]

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 27365971-(3-Hydroxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 584994803-(4-Isopropyl-piperazin-1-yl)-phenolYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetone (1.95 g) and NaBH(OAc)3 (7.12 g) were added to a solution of 3-piperazin-1-yl-phenol (2.00 g) in THF (40 ml), and the mixture was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and filtered to give the titled compound (1.48 g, colorless powder).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f0cc949488174e2aa69b178879108f42
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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