(S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)-4-((R)-1-phenylethyl)morpholine → (2S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)morpholine

HRID 424422Notes

Reaction equation

HRID 424422 reaction equation
[CH:1]1([N:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C@@H](C4C=CC=CC=4)C)[CH2:16]3)=[CH:11][CH:10]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].C(O)C>[CH:1]1([N:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:11][CH:10]=2)[CH3:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 66703943(S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)-4-((R)-1-phenylethyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 66704002(2S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)morpholineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A 300-ml flask containing a solution of (S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)-4-((R)-1-phenylethyl)morpholine (7.27 g, 19.07 mmol) and 10% palladium on carbon (3.0 g) in ethanol (30 ml) was charged with hydrogen. The reaction mixture was stirred vigorously at 50° C. for 10 hours. The catalyst was filtered off with a Celite pad, and the filtrate was concentrated under reduced pressure to yield (2S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)morpholine (4.95 g, 95%) as a clear oil.

Workup

  1. filtrationThe catalyst was filtered off with a Celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e77c92184e04ea2b195d40fb0c901e4
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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