Water → 4-(4-Bromobenzyl)morpholine

HRID 1978686Notes

Reaction equation

HRID 1978686 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.O>CN(C=O)C>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 685274-Bromobenzyl bromide

Product 1

HCID 7835034-(4-Bromobenzyl)morpholineYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In DMF (108 ml) was dissolved morpholine (9.0 g). To the mixture were added at room temperature triethylamine (24 ml) and 4-bromobenzyl bromide (21.5 g), and the mixture was stirred at 80° C. for 16 hours and cooled to room temperature. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=2/1) to give 4-(4-bromobenzyl)morpholine (17.2 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ba8af837ec1e48c4a74b4db4e6ba1b32
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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