HCID 69352738, compound → HCID 69351642, compound

HRID 1609807Notes

Reaction equation

HRID 1609807 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 69352738HCID 69352738, compound

Product 1

HCID 69351642HCID 69351642, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-(3S)-3-(4-nitrophenoxy)piperidine (6.5 g) and 1.2 g of 10% Pd/C in methanol (30 mL) was subjected to hydrogenation (50 psi). When the reaction was completed, the reaction mixture was filtered. The filtrate was concentrated in vacuo, giving a yellow solid. Recrystallization in CH2Cl2/hexane afforded (3S)-3-(4-aminophenoxy)piperidine (3.5 g, 88% yield) as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customgiving a yellow solid
  4. customRecrystallization in CH2Cl2/hexane

Sources & evidence

ORD record
ord-4a5277ee83574ceaba841b2fb2b03de7
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

Loading…