1-Bromo-3-chloropropane → 4-(3-Chloropropyl)morpholine

HRID 1925342Notes

Reaction equation

HRID 1925342 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].C(=O)([O-])[O-].[K+].[K+].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CN(C=O)C.O>[Cl:5][CH2:4][CH2:3][CH2:2][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8083MorpholineHCID 11430Potassium Carbonate

Product 1

HCID 958344-(3-Chloropropyl)morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-3-chloropropane (3.4 mL, 34.5 mmol) in DMF (40 mL), was added potassium carbonate (6.4 g, 69 mmol) and morpholine (2.0 mL, 23.0 mmol). The solution was stirred at RT for 15 h, then diluted with H2O (150 mL). The mixture was extracted with EtOAc (3×25 mL) and the organic extracts were washed with H2O and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give title compound as a colorless oil. MS (ESI, pos. ion) m/z: 164 (M+1). Mass Calc'd for C7H14ClNO: 163.08.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×25 mL)
  2. washthe organic extracts were washed with H2O and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f1793eee2b94fcca71fd9eec5941808
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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