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

HRID 2282231Notes

Reaction equation

HRID 2282231 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 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of morpholine (2.00 g, 23.0 mmol) in toluene (200 mL), was added 1-bromo-3-chloropropane (4.55 mL, 45.9 mmol) and the mixture was stirred for 4 h at 70° C. Insoluble materials were removed by filtration and the filtrate has been concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=70/30→100/0) to give the title compound (1.27 g, 68%) as a colorless oil.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate has been concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=70/30→100/0)

Sources & evidence

ORD record
ord-1c348d990a234575866a1cee8db26a99
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…