Morpholine → 4-(3-phenoxypropyl)Morpholine

HRID 411605Notes

Reaction equation

HRID 411605 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[O:1]([CH2:8][CH2:9][CH2:10][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 14798Sodium HydroxideHCID 68522Benzene, (3-bromopropoxy)-2×

Product 1

HCID 20574374-(3-phenoxypropyl)Morpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[3-(Phenoxy)propyl] morpholine was prepared by a reaction of 3-(phenoxy)propyl bromide with morpholine. For example, 3-(phenoxy)propyl bromide (7.8 ml, 50 mmole) was added to morpholine (8 ml) in toluene (50 ml) and refluxed overnight. NaOH solution (2 g of NaOH in 20 ml of water) was added and additionally refluxed for 4 hr. Toluene was removed by distillation under reduced pressure. Residue was treated with dichloromethane(200 ml) and water(200 ml). Dichloromethane layer was dried and concentrated. Residue was treated with dichloromethane-heptane to give 7 g of 4-[3-(phenoxy)propyl] morpholine.

Workup

  1. temperaturerefluxed overnight
  2. temperatureadditionally refluxed for 4 hr
  3. customToluene was removed by distillation under reduced pressure
  4. additionResidue was treated with dichloromethane(200 ml) and water(200 ml)
  5. dry with materialDichloromethane layer was dried
  6. concentrationconcentrated
  7. additionResidue was treated with dichloromethane-heptane

Sources & evidence

ORD record
ord-5105b4c3530b4fb4af23ef65b8cbd273
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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