(+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine → 3-Benzo[1,3]dioxol-5-ylmethyl-piperidine

HRID 2354564Notes

Reaction equation

HRID 2354564 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13](CC4C=CC=CC=4)[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 68451530(+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

Product 1

HCID 170395273-Benzo[1,3]dioxol-5-ylmethyl-piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.40 g (4.5 mmol) of (+)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine is dissolved in 35 ml MeOH and 1 ml AcOH and hydrogenated over Pd/C 10% (0.3 g) for 2 d until hydrogen absorption is complete. The mixture is filtered over Celite®, and the filtrate is evaporated, diluted with CH2Cl2, washed with sat. aq. Na2CO3 solution and evaporated to give (+)-3-benzo[1,3]dioxol-5-ylmethyl-piperidine ([α]Drt=5.90 (c=0.5, DMSO)) which is used without further purification.

Workup

  1. custom1 ml AcOH and hydrogenated over Pd/C 10% (0.3 g) for 2 d until hydrogen absorption
  2. filtrationThe mixture is filtered over Celite®
  3. customthe filtrate is evaporated
  4. additiondiluted with CH2Cl2
  5. washwashed with sat. aq. Na2CO3 solution
  6. customevaporated

Sources & evidence

ORD record
ord-e6282ada6480498a9f7db1b50b815a7a
Source dataset
uspto-grants-2010_07
Patent number
US07754719B2

Reaction notes

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