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

HRID 2203517Notes

Reaction equation

HRID 2203517 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 allowed to warm to ambient temperature. Dichloromethane was added, and the resulting solution was washed with water, 1N aqueous hydrogen chloride, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 4-(2-bromoacetyl)morpholine as a colorless oil.

Workup

  1. additionAfter the addition
  2. temperatureto warm to ambient temperature
  3. washthe resulting solution was washed 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-66e98a248e9e43a880b1cca546b1c8c2
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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