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

HRID 1791517Notes

Reaction equation

HRID 1791517 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][CH2:10][Cl:11]>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

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 8083Morpholine

Product 1

HCID 958344-(3-Chloropropyl)morpholineYield 77.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Morpholine (52.2 ml, 600 mmol) and 1-bromo-3-chloropropane (30 ml, 300 mmol) were dissolved in dry toluene (180 ml) and heated to 70° C. for 3 hours. The solid was removed by filtration and the filtrate evaporated under vacuum. The resulting oil was decanted from the additional solid residue and the oil was vacuum distilled to yield 1-chloro-3-morpholinopropane (37.91 g, 77%) as an oil.

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate evaporated under vacuum
  3. customThe resulting oil was decanted from the additional solid residue
  4. distillationdistilled

Sources & evidence

ORD record
ord-67df1fd40f8a49ee96ddc5e8b3355166
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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