4-Benzyl-2-(3-methoxyphenyl)morpholine → 2-(3-Methoxyphenyl)morpholine

HRID 530608Notes

Reaction equation

HRID 530608 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 1178704194-Benzyl-2-(3-methoxyphenyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 242715162-(3-Methoxyphenyl)morpholineYield 56.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

In a 250 mL round-bottomed flask, 4-benzyl-2-(3-methoxyphenyl)morpholine (2.3 g, 8.12 mmol) and palladium hydroxide on carbon (285 mg, 406 μmol) were combined in methanol (15 ml). The suspension was stirred at room temperature under a balloon of hydrogen overnight. The system was evacuated with argon 3 times. The reaction mixture was filtered through Celite, and the filtercake washed several times with methanol. The combined filtrate and washes were concentrated in vacuo to afford 2-(3-methoxy-phenyl)-morpholine (0.88 g, 56%) which was directly used for next step. (M+H)+=194 m/e.

Workup

  1. customThe system was evacuated with argon 3 times
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filtercake washed several times with methanol
  4. concentrationThe combined filtrate and washes were concentrated in vacuo

Sources & evidence

ORD record
ord-b0a6f456346b4cc19cd8cfca81809cf3
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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