Chloroacetamide → HCID 15544537, compound

HRID 1883957Notes

Reaction equation

HRID 1883957 reaction equation
Cl[CH2:2][C:3]([NH2:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[CH:27][C:28]([OH:33])=[C:29]([CH:32]=2)[CH:30]=O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1CCCC1=O>[CH2:12]([N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:26]=[CH:27][C:28]3[O:33][C:2]([C:3]([NH2:5])=[O:4])=[CH:30][C:29]=3[CH:32]=2)[CH2:23][CH2:24]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 23508725HCID 23508725, compound

Product 1

HCID 15544537HCID 15544537, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

10 ml of 1-methyl-2-pyrrolidone, 0.4 g of chloroacetamide and 0.8 g of potassium carbonate are added at 20° C. with stirring/under nitrogen to 1.0 g of 5-(4-benzylpiperazin-1-yl)-2-hydroxybenzaldehyde. The mixture is stirred at 60° C. for 16 hours, cooled and then filtered, and the solvent is removed under reduced pressure. The residue is taken up in MTB ether, re-filtered and concentrated, and the residue is crystallized from toluene. The isolated yield is 0.73 g (65%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customthe solvent is removed under reduced pressure
  4. filtrationre-filtered
  5. concentrationconcentrated
  6. customthe residue is crystallized from toluene

Sources & evidence

ORD record
ord-87f71c74a74b4156844dc3f23f6e8082
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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