4-Benzyl-2-(4-octyloxy-phenyl)-morpholine → 2-(4-Octyloxy-phenyl)-morpholine

HRID 2167872Notes

Reaction equation

HRID 2167872 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:19][CH:18]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 1

HCID 670323994-Benzyl-2-(4-octyloxy-phenyl)-morpholine

Product 1

HCID 670323512-(4-Octyloxy-phenyl)-morpholineYield 95.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-2-(4-octyloxy-phenyl)-morpholine (20.22 g; 53 mmol) in MeOH (400 mL) was added palladium hydroxide (0.74 g; 5.30 mmol). The mixture was treated with H2, at normal pressure, overnight. The reaction mixture was filtered over Kieselguhr. The filter-cake was washed with a solution of ammonia in MeOH. Evaporation of the solvent afforded 2-(4-octyloxy-phenyl)-morpholine (14.80 g), which was used as such in the next step.

Workup

  1. additionThe mixture was treated with H2, at normal pressure, overnight
  2. filtrationThe reaction mixture was filtered over Kieselguhr
  3. washThe filter-cake was washed with a solution of ammonia in MeOH
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-28644eb698fc409cbf1944bf60296537
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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