Benzaldehyde → 1-Benzylpiperidin-3-ol

HRID 2035525Notes

Reaction equation

HRID 2035525 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 232933-HydroxypiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 857731-Benzylpiperidin-3-olYield 49%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

943 mg of 3-hydroxypiperidine was dissolved in 15 mL of toluene, to which, under ice cooling, 1.13 mL of benzaldehyde, 2.97 g of sodium triacetoxyborohydride and 0.3 mL of acetic acid were sequentially added, and stirred at room temperature for 24 hours. To the reaction mixture, saturated sodium bicarbonate was added, extracted with ethyl acetate, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (chloroform to chloroform:methanol-ammonia=60:1) to obtain 866.3 mg (49%) of 1-benzyl-3-hydroxypiperidine crude product as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography (chloroform to chloroform:methanol-ammonia=60:1)

Sources & evidence

ORD record
ord-7ed27702d1fb455bbf69a4dbec9aa0db
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

Loading…