4-Benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine → 2-(4-Phenethyl-phenyl)-morpholine

HRID 2167873Notes

Reaction equation

HRID 2167873 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]3[C:27](Cl)=[CH:26][CH:25]=[CH:24][C:23]=3Cl)=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH2:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:15][CH:16]=1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 670323004-Benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine

Product 1

HCID 670324382-(4-Phenethyl-phenyl)-morpholineYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine (0.54 g; 1.27 mmol) and palladium hydroxide (0.04 g; 0.25 mmol) in MeOH (25 mL) was treated with H2, at normal pressure, overnight. The resulting mixture was filtered over Kieselguhr and the solvents evaporated to afford 2-(4-phenethyl-phenyl)-morpholine (0.34 g).

Workup

  1. additionwas treated with H2, at normal pressure, overnight
  2. filtrationThe resulting mixture was filtered over Kieselguhr
  3. customthe solvents evaporated

Sources & evidence

ORD record
ord-555ab81379184e119f1e54089d641871
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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