Water → Ethyl 4-(2,5-dichlorobenzyl)piperazine-1-carboxylate

HRID 2184832Notes

Reaction equation

HRID 2184832 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]Cl.[CH2:11]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][N:19]1[CH2:18][CH2:17][N:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 759762,5-Dichlorobenzyl chloride

Product 1

HCID 22458123Ethyl 4-(2,5-dichlorobenzyl)piperazine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichlorobenzyl chloride (2.01 g) was added to a mixture of 1.94 g of 1-ethoxycarbonylpiperazine and 3.45 g of anhydrous potassium carbonate in 20 ml of N,N-dimethylformamide stirred at room temperature in nitrogen atmosphere. After 24 h of stirring at the same temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase, which was dried on anhydrous Na2SO4, was evaporated to dryness under vacuum. The oily residue was purified via flash chromatography (petrolium ether-ethyl acetate 85:15) giving 2 g (63%) of the title compound.

Workup

  1. stirringAfter 24 h of stirring at the same temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase, which was dried on anhydrous Na2SO4
  4. customwas evaporated to dryness under vacuum
  5. customThe oily residue was purified via flash chromatography (petrolium ether-ethyl acetate 85:15)

Sources & evidence

ORD record
ord-4d42814bec4e48b4b2a0f94eaea3083e
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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