Dimethylformamide → 5-Cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one

HRID 579171Notes

Reaction equation

HRID 579171 reaction equation
[CH:1]1([CH:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CN([CH:19]=[O:20])C>>[CH:1]1([CH:7]2[N:12]([CH2:7][C:1]3[CH:6]=[CH:5][C:4]([O:20][CH3:19])=[CH:3][CH:2]=3)[C:11](=[O:13])[CH2:10][O:9][CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 666839435-Cyclohexyl-morpholin-3-one

Product 1

HCID 666847235-Cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-oneYield 91%

Procedure

To a solution of 5-Cyclohexyl-morpholin-3-one (1.0 g, 5.5 mmol, 1.0 equiv) in DMF (15.0 mL) at 0° C. was added NaH (0.26 g, 60% in oil, 6.5 mmol, 1.2 equiv) slowly. The mixture was stirred at room temperature for 30 minutes, then it was added PMBCI (0.94 g, 6.0 mmol, 1.1 equiv). After stirred at room temperature for 2 hours, the reaction mixture was quenched by added to sat. aq. NH4Cl solution. The mixtures were extracted with EtOAc. The organic layers were combined and washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel, acetone/heptane 30% to give 1.5 g (91%) of 5-Cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one.

Workup

  1. additionit was added PMBCI (0.94 g, 6.0 mmol, 1.1 equiv)
  2. stirringAfter stirred at room temperature for 2 hours
  3. customthe reaction mixture was quenched
  4. additionby added to sat. aq. NH4Cl solution
  5. extractionThe mixtures were extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel, acetone/heptane 30%

Sources & evidence

ORD record
ord-edd9549087284078baa453a3b015790e
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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