Morpholine → 3-(4-Bromophenyl)-1-morpholinopropan-1-one

HRID 931513Notes

Reaction equation

HRID 931513 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](Cl)=[O:17])=[CH:10][CH:9]=1>ClCCl.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:17])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 224116513-(4-Bromophenyl)propanoyl chloride

Product 1

HCID 221798563-(4-Bromophenyl)-1-morpholinopropan-1-oneYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of morpholine (11 g, 126.44 mmol, 2.01 equiv) in dichloromethane (60 mL) 0˜5° C. was added a solution of 3-(4-bromophenyl)propanoyl chloride (15.5 g, 63.01 mmol, 1.00 equiv) in dichloromethane (30 mL) dropwise with stirring. The resulting solution was stirred at 0˜5° C. for 1 h. The reaction mixture was warmed to room temperature. The resulting solution was diluted with 40 mL of water. The mixture was extracted with dichloromethane 2×100 mL. The combined organic layers was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 17.4 g (93%) of 3-(4-bromophenyl)-1-morpholinopropan-1-one as a white solid.

Workup

  1. stirringThe resulting solution was stirred at 0˜5° C. for 1 h
  2. extractionThe mixture was extracted with dichloromethane 2×100 mL
  3. washThe combined organic layers was washed with 3×50 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d449dca5a59c4195a6eb917b7c05b4fc
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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