Sodium borohydride → [4-(Piperidine-1-carbonyl)phenyl]methanol

HRID 1957180Notes

Reaction equation

HRID 1957180 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190690894-(Piperidine-1-carbonyl)benzaldehyde

Product 1

HCID 11644226[4-(Piperidine-1-carbonyl)phenyl]methanolYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The aldehyde (28.6 mmol) thus formed was dissolved in 40 mL of absolute ethanol, and 540 mg NaBH4 was added over 2 hours. When thin-layer chromatography revealed no remaining aldehyde, the reaction was quenched with 2.5 mL acetic acid. The ethanol was removed on a rotary evaporator and the residue was taken up in 30 mL water. The product alcohol was extracted with two 25-mL volumes of CH2Cl2 plus 25 mL ether. The organic extracts were combined and dried over Na2SO4. Removal of the solvents on a rotary evaporator yielded 4.08 g of 1-(4'-hydroxymethylbenzoyl)piperidine, which was collected by filtration and washed with petroleum ether. The product (Compound IV, 1-(4'-hydroxymethylbenzoyl)piperidine) had a melting point of 119.6°-122.7° C. 1H NMR showed the methylene protons at 4.715 (2H, d, J=5.5 Hz) ppm.

Workup

  1. customthe reaction was quenched with 2.5 mL acetic acid
  2. customThe ethanol was removed on a rotary evaporator
  3. extractionThe product alcohol was extracted with two 25-mL volumes of CH2Cl2 plus 25 mL ether
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvents
  6. customon a rotary evaporator

Sources & evidence

ORD record
ord-8b9184fc036946c8809db79235bf4142
Source dataset
uspto-grants-1998_07
Patent number
US05783587

Reaction notes

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