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

HRID 2276826Notes

Reaction equation

HRID 2276826 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>C1(C)C=CC=CC=1>[Cl:5][CH2:4][CH2:3][CH2:2][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 8083Morpholine

Product 1

HCID 958344-(3-Chloropropyl)morpholineYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-bromo-3-chloropropane (10.0 g, 63.5 mmol) in toluene (100 mL) was added morpholine (11.0 mL, 127 mmol). The mixture was stirred under reflux conditions for 2 h, then was filtered. The filtrate was washed with water and the organic layer was dried, concentrated in vacuo, then distilled to afford 45 (10.0 g, 96%). 1H NMR (300 MHz, DMSO-d6): δ 3.70-3.80(m, 4H), 3.60 (t, 2H), 2.40-2.60(m, 6H), 1.90 (m, 2H). MS (M+H): 164.

Workup

  1. filtrationwas filtered
  2. washThe filtrate was washed with water
  3. customthe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. distillationdistilled

Sources & evidence

ORD record
ord-e6b7819b745246daa487544fc486148d
Source dataset
uspto-grants-2015_09
Patent number
US09133137B2

Reaction notes

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