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

HRID 2383584Notes

Reaction equation

HRID 2383584 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+]>CCO>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(4-bromophenyl)piperidin-4-one (600 mg, 2.36 mmol) in EtOH (10 mL) was added NaBH4 (134 mg, 3.54 mmol) slowly at 0° C. The resulting mixture was stirred at rt for 1 h. The reaction was quenched with sat. NH4Cl solution, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to dryness. The title compound was isolated by silica gel chromatography (EtOAc/hexanes, 2:3 to 3:2) as a yellow solid (606 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=8.9 Hz, 2H), 6.81 (d, J=8.9 Hz, 2H), 3.89-3.84 (m, 1H), 3.55-3.49 (m, 2H), 2.95-2.89 (m, 2H), 2.06-1.99 (m, 2H), 1.72-1.64 (m, 2H); MS ESI 255.9 [M+H]+, calcd for [C11H14BrNO+H]+ 256.03.

Workup

  1. customThe reaction was quenched with sat. NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2abd2b16b4af414da52aaedbd7b7952b
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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