Chloroacetyl chloride → 2-Chloro-1-(2,6-dimethyl-morpholin-4-yl)-ethanone

HRID 1971829Notes

Reaction equation

HRID 1971829 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Cl:9][CH2:10][C:11](Cl)=[O:12]>CCOCC>[Cl:9][CH2:10][C:11]([N:4]1[CH2:5][CH:6]([CH3:8])[O:7][CH:2]([CH3:1])[CH2:3]1)=[O:12]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 1108622,6-Dimethylmorpholine

Product 1

HCID 41439202-Chloro-1-(2,6-dimethyl-morpholin-4-yl)-ethanoneYield 47.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,6-Dimethylmorpholine (a mixture of trans- and cis-isomers (1.0 g, 8.7 mmol) and TEA (1.34 ml, 9.6 mmol) were dissolved in anhydrous ether (50 ml) and cooled in ice bath. To the above mixture was added dropwise a solution of chloroacetyl chloride (0.69 ml, 8.7 mmol). Then the mixture was warmed to room temperature and stirred for 3 hours. The mixture was washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography (EA/PE=1/1) to afford the title compound (0.79 g, yield 47.5%).

Workup

  1. temperaturecooled in ice bath
  2. washThe mixture was washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography (EA/PE=1/1)

Sources & evidence

ORD record
ord-c21d03ba6b9647749c821fc02aae8652
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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