Monobenzone → 4-[2-(Benzyloxy-phenoxy)-ethyl]-morpholine

HRID 2097357Notes

Reaction equation

HRID 2097357 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C([O-])([O-])=[O:27].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:27][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 29954124-[2-(Benzyloxy-phenoxy)-ethyl]-morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

4-Benzyloxyphenol (4.0 g, 20 mmol), chloroethylmorpholine hydrochloride (3.72 g, 20 mmol) and K2CO3 (5.53 g, 40 mmol) were suspended in DMF (50 mL) under an atmosphere of argon and stirred at 105° C. for 17 h. The solvent was removed under reduced pressure and the residue was partitioned between water (80 mL) and Et2O (150 mL). The aqueous layer was extracted with Et2O (1×30 mL), the combined org. layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0-10% MeOH in EtOAc) to give the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water (80 mL) and Et2O (150 mL)
  3. extractionThe aqueous layer was extracted with Et2O (1×30 mL)
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-049e88233e0f4d108aa493aa8d475de7
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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