Chloroacetyl chloride → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}chloroacetamide

HRID 545103Notes

Reaction equation

HRID 545103 reaction equation
Cl.Cl.[NH2:3][CH2:4][C@@H:5]1[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:6]1.C(=O)([O-])O.[Na+].[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)(Cl)Cl>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:7]1[CH2:8][CH2:9][O:10][C@@H:5]([CH2:4][NH:3][C:27](=[O:28])[CH2:26][Cl:25])[CH2:6]1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 57464066(S)-(4-(3,4-Dichlorobenzyl)morpholin-2-yl)methanamine dihydrochloride

Product 1

HCID 57686783(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}chloroacetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(2S)-2-Aminomethyl-4-(3,4-dichlorobenzyl)morpholine dihydrochloride (30.5 g) was added to chloroform (400 mL) and saturated aqueous sodium hydrogen carbonate solution (400 mL). After dropwise addition of chloroacetyl chloride (7.7 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. After completion of the reaction, the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (31.6 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bd704917961b4d369760bc3b96598b7e
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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