Acetaldehyde → Phenyl-piperidin-4-yl-methanol

HRID 1058778

Reaction equation

HRID 1058778 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)C.[OH-].[Na+].[Na+].[Cl-]>ClCCl>[C:2]1([CH:1]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 226102Phenyl(piperidin-4-yl)methanone

Product 1

HCID 339086Phenyl-piperidin-4-yl-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
3.5 °C

Procedure

4-benzoyl-piperidine (2.0 g, 10.6 mmol) was added over a solution of 6.8 g of (+)-B-chlorodiisopinocanfeilboran ((+)-DIP-Cl) (21.25 mmol) in dichloromethane (20 mL, dry) cooled down to 3-4° C. After reacting for 72 h, 2.0 mL of acetaldehyde (35.46 mmol) were added and stirred at room temperature for 3 h. 24 mL of an aqueous NaOH (6N) solution, dichloromethane and saturated aqueous NaCl solution were added. The phases were separated and the usual treatment of the organic phase provided (+)-α-phenyl4-piperidinemethanol as a white solid with a m.p.=64-66° C. in a 90% yield (84% ee).

Workup

  1. customThe phases were separated

Sources & evidence

ORD record
ord-5b340ce48bb34c8c824d98daaba40a8a
Source dataset
uspto-grants-2003_02
Patent number
US06518284B2

Linked notes

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