Morpholine → 1-(3-Morpholin-4-yl-phenyl)propan-1-one

HRID 2307420Notes

Reaction equation

HRID 2307420 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(OC(C)(C)C)(C)(C)C.[Na]>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:12]1([C:2]2[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 882721-Propanone, 1-(3-bromophenyl)-HCID 86662868Sodium t-butyloxide

Product 1

HCID 226056081-(3-Morpholin-4-yl-phenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3′-bromopropiophenone (11.4 g, 53 mmol), morpholine (60 mL), palladium acetate (300 mg, 2.5 mol %), di-t-butyl-biphenylphosphine (800 mg, 5 mol %), sodium t-butyloxide (6.1 g, 64 mmol) was stirred at 80° C. in a sealed tube for 24 hours. After cooling down, the reaction mixture was diluted with dichloromethane (150 mL) and washed with water (50 mL). The aqueous layer was extracted with dichloromethane (2×75 mL) and the combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography of Biotage with 25% ethyl acetate/hexanes to provide the title compound as pale yellow clear oil (4.23 g,).

Workup

  1. temperatureAfter cooling down
  2. washwashed with water (50 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×75 mL)
  4. dry with materialthe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography of Biotage with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d36b342479014b90b6e4c58c10f778fc
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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