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

HRID 2233235Notes

Reaction equation

HRID 2233235 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH:8]=[CH:9][CH2:10][Cl:11].BrCCCCl>C1(C)C=CC=CC=1>[Cl:11][CH2:10][CH2:9][CH2:8][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8083MorpholineHCID 30159301-Propene, 1-bromo-3-chloro-

Product 1

HCID 958344-(3-Chloropropyl)morpholineYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of morpholine (261 ml, 3.00 mol) and 1-bromo-3-chloropropene (148 ml, 1.50 mol) in toluene (900 ml) was stirred for 18 hours at ambient temperature. Additional 1-bromo-3-chloropropane (25 ml, 0.25 mol) was added, the reaction was stirred for a further 1 hour and then filtered to remove the precipitated solid before the filtrate was concentrated in vacuo. Distillation of the crude oil yielded N-(3-chloropropyl)-morpholine (119.3 g, 49% yield) as the fraction boiling at 70-80° C./2.6 mmHg:

Workup

  1. stirringthe reaction was stirred for a further 1 hour
  2. filtrationfiltered
  3. customto remove the precipitated solid before the filtrate
  4. concentrationwas concentrated in vacuo
  5. distillationDistillation of the crude oil

Sources & evidence

ORD record
ord-eb5c374e58a245c4a4df052e979a4c7d
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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