Hydrochloric Acid → 1,3-Dibenzylpiperidin-4-one

HRID 362546Notes

Reaction equation

HRID 362546 reaction equation
C([C:5]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)(OC)=O.Cl>CO>[CH2:12]([N:7]1[CH2:8][CH2:9][C:10](=[O:11])[CH:5]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 542328573-Carbomethoxy-1,3-dibenzyl-4-piperidone

Product 1

HCID 230036591,3-Dibenzylpiperidin-4-oneYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-carbomethoxy-1,3-dibenzyl-4-piperidone (0.61 g, 1.78 mmol), MeOH (10 mL) and 5M HCl aq. (25 mL, 125 mmol) was refluxed overnight. The reaction mixture was concentrated and chromatographed (silica gel, eluting with 4:1 hexane-EtOAc) to give 1,3-dibenzyl-4-piperidone (0.31 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed
  3. wash(silica gel, eluting with 4:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-f145b1af83a546b4a75ea44357d436b1
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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