4-Benzyl-2-(4-benzyloxy-phenyl)-morpholine → 4-(Morpholin-2-yl)phenol

HRID 588244Notes

Reaction equation

HRID 588244 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]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[NH:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 666537174-Benzyl-2-(4-benzyloxy-phenyl)-morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 538045794-(Morpholin-2-yl)phenolYield 96.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-2-(4-benzyloxy-phenyl)-morpholine (8.35 g; 23.2 mmol) in MeOH (100 mL) was added a catalytic amount of palladium hydroxide (0.65 g; ˜20 wt % on carbon, wet). The resulting mixture was treated with hydrogen (1 atm.) at RT, overnight. Subsequently, the mixture was filtered over kieselguhr, rinsed with MeOH, and concentrated in vacuo to afford 4-morpholin-2-yl-phenol (4.00 g), which was used as such.

Workup

  1. filtrationSubsequently, the mixture was filtered over kieselguhr
  2. washrinsed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a0882689c4c4d8790eccf17fcfb4b02
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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