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

HRID 22775

Reaction equation

HRID 22775 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>[O:4]1[CH2:5][CH2:6][N:1]([CH2:8][CH2:9][CH2:10][Cl:11])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 8083Morpholine

Product 1

HCID 958344-(3-Chloropropyl)morpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of morpholine (52.2 ml), 1-bromo-3-chloropropane (30 ml) and toluene (180 ml) was heated to 70° C. for 3 hours. The solid was removed by filtration and the filtrate was evaporated under vacuum. The resultant oil was decanted from the additional solid which was deposited and the oil was purified by vacuum distillation to yield 3-morpholinopropyl chloride (37.91 g); NMR Spectrum: (DMSOd6) 1.85 (m, 2H), 2.3 (t, 4H), 2.38 (t, 2H), 3.53 (t, 4H), 3.65 (t, 2H).

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated under vacuum
  3. customThe resultant oil was decanted from the additional solid which
  4. distillationthe oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-a049d93aa79344ffb2fda0463cf54c65
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Linked notes

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