Chloroacetyl chloride → HCID 14053698, compound
Reaction equation
[NH:1]1[CH:5]([C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])[CH2:4][CH2:3][C:2]1=[O:14].C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[NH:1]1[CH:5]([C:6]([N:8]2[CH2:9][CH2:10][N:11]([C:23](=[O:24])[CH2:22][Cl:21])[CH2:12][CH2:13]2)=[O:7])[CH2:4][CH2:3][C:2]1=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixed solution of 2.3 g of N-(2-pyrrolidone-5-carbonyl)piperazine, 50 ml of methylene chloride, and 2.8 g of anhydrous potassium carbonate was cooled with ice water and 1.3 g of chloro acetyl chloride was dropped therein with stirring. After the dropping, the mixture was stirred for another 1 hour at room temperature. The insoluble matter was removed by filtration and the solvent was evaporated in vacuo from the filtrate to give 2.3 g of oily N-(2-pyrrolidone-5-carbonyl)-N'-chloroacetylpiperazine. This was dissolved in 15 ml of N,N-dimethylformamide and 0.8 g of morpholine and 2.2 g of anhydrous potassium carbonate were added thereto, and the mixture was heated at 80° C. for 3 hours with stirring. The insoluble matter was filtered off therefrom and the solvent was evaporated in vacuo from the filtrate. The residue was purified by a silica gel column chromatography to give 2.5 g of the product. This was recrystallized from a mixture of methanol and ethyl ether to give 2.1 g of desired product, m.p. 204°-205° C.
Workup
- additionwas dropped
- stirringAfter the dropping, the mixture was stirred for another 1 hour at room temperature
- customThe insoluble matter was removed by filtration
- customthe solvent was evaporated in vacuo from the filtrate
Sources & evidence
- ORD record
- ord-3152a1fc83ac428b87769ac3541529f4
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05102882
Reaction notes
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