1-Chloroethyl chloroformate → HCID 22999321, compound

HRID 1166753Notes

Reaction equation

HRID 1166753 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[C:5]([CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14](CC2C=CC=CC=2)[CH2:13][CH2:12]1.Cl[C:25]([O:27][CH:28]([Cl:30])[CH3:29])=[O:26].CCCCCC.CCOC(C)=O>ClCCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[C:5]([CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([C:25]([O:27][CH:28]([Cl:30])[CH3:29])=[O:26])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 5213051-Chloroethyl chloroformateHCID 2052444HCID 2052444, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 22999321HCID 22999321, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The 4-(2,5-dimethyl-4-formylphenyl)-1-benzylpiperazine (9 g, 29 mmol) was dissolved in anhydrous 1,2-dichloroethane (100 mL) and 1-chloroethyl chloroformate (4.5 g, 31.5 mmol) was added. The solution was refluxed for 30 minutes or until TLC analysis indicated the disappearance of the starting material. The product was just slightly less polar than the starting material by TLC using hexane/EtOAc (3/1). Dichloroethane was evaporated and the residue was chromatographed using gradient hexane/EtOAc (10/0 to 8/2) to give the product (6 g, 64%) as an oil.

Workup

  1. temperatureThe solution was refluxed for 30 minutes or until TLC analysis
  2. customDichloroethane was evaporated
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-8133b2c74c80437ebd33b983bc4ed46d
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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