Bis(2-chloroethyl) ether → 4-(3-Methoxyphenyl)morpholine

HRID 349680

Reaction equation

HRID 349680 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.Cl[CH2:11][CH2:12][O:13][CH2:14][CH2:15]Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 108243-Methoxyaniline

Product 1

HCID 99643354-(3-Methoxyphenyl)morpholineYield 77.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of m-anisidine (11.2 mL, 0.1 mol), chloroethyl ether (11.7 mL, 0.1 mol), and diisopropylethylarine (35 mL, 0.2 mol) in toluene (100 mL) was stirred at reflux for 72 h. The precipitate was removed by filtration and washed with toluene (100 mL). The combined toluene solutions were concentrated in vacuo and purified by distillation (120–130° C., 0.2 Torr) to afford the intermediate 4-(3-methoxyphenyl)-morpholine (14.9 g, 77%).

Workup

  1. temperatureat reflux for 72 h
  2. customThe precipitate was removed by filtration
  3. washwashed with toluene (100 mL)
  4. concentrationThe combined toluene solutions were concentrated in vacuo
  5. distillationpurified by distillation (120–130° C., 0.2 Torr)

Sources & evidence

ORD record
ord-7d679226bb9f4cc49a0bf6f5f638a0ef
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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