Sodium Bicarbonate → 1-(4-Bromophenyl)piperidin-4-ol

HRID 715560Notes

Reaction equation

HRID 715560 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 246921481-(4-Bromophenyl)piperidin-4-one

Product 1

HCID 235052161-(4-Bromophenyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Bromophenyl)piperidin-4-one (765 mg) is dissolved under argon in MeOH (8 mL), cooled to 0° C. and treated with NaBH4 (145 mg). The mixture is stirred for 2 hours at 0° C., treated with saturated aqueous NaHCO3 solution and stirred for 10 minutes. Then the mixture is extracted with ethylacetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated to give the title compound. LC (method 2): tR=0.92 min; Mass spectrum (ESI+): m/z=256 [M+H]+.

Workup

  1. stirringstirred for 10 minutes
  2. extractionThen the mixture is extracted with ethylacetate
  3. washthe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents are evaporated

Sources & evidence

ORD record
ord-3d95ece6ff234f99847e4c9a3d22fdb0
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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