Morpholine → 2-Bromo-1-(morpholin-4-yl)ethan-1-one

HRID 419294Notes

Reaction equation

HRID 419294 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>ClCCl>[Br:1][CH2:2][C:3]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:4]

Participants

4

Conditions

Temperature
-25 °C

Procedure

A solution of bromoacetyl bromide (3.0 mL, 0.034 mol) in dichloromethane (240 mL) was cooled to −25° C. A solution of morpholine (9.0 mL, 0.10 mol) in dichloromethane (20 mL) was slowly added over a period of one hour. After the addition was complete, the reaction was stirred at −25° C. for 15 minutes and then allowed to warm to ambient temperature. Dichloromethane was added, and the resulting solution was washed sequentially with water, 1N aqueous hydrogen chloride, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 4-(bromoacetyl)morpholine as a colorless oil.

Workup

  1. additionAfter the addition
  2. temperatureto warm to ambient temperature
  3. washthe resulting solution was washed sequentially with water, 1N aqueous hydrogen chloride, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationand concentrated under reduced pressure

Sources & evidence

ORD record
ord-46ff5e18069b4b4788d4d3158ba28158
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Reaction notes

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