1-Chloroethyl chloroformate → HCID 53930236, compound

HRID 1059366Notes

Reaction equation

HRID 1059366 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 54442297HCID 54442297, compound

Product 1

HCID 53930236HCID 53930236, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1.6 g of ethyl 3-(1-benzylpiperidin-4-yl)propenoate in 1,2-dichloroethane (30 ml) was added at 0° C. 0.74 ml of 1-chloroethyl chloroformate and the resulting mixture was stirred at the same temperature for 15 minutes and then heated under reflux for 1 hour. After distilling off the solvent under reduced pressure, 50 ml of methanol was added to the residue and the resulting mixture was heated under reflux for 1 hour. Then the mixture was made weakly alkaline with a dilute aqueous solution of sodium hydroxide and the solvent was distilled off under reduced pressure. To a solution of 1.0 g of ethyl 3-(piperidin-4-yl)propenoate thus obtained and 0.64 g of 8-(chloroethyl)-1OH-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (30 ml) was added 1.1 g of anhydrous potassium carbonate and the resulting mixture was stirred by heating to 60° C. for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with methanol/dichloromethane) to thereby give 0.6 g of the title compound as yellow crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. distillationAfter distilling off the solvent under reduced pressure, 50 ml of methanol
  4. additionwas added to the residue
  5. temperaturethe resulting mixture was heated
  6. temperatureunder reflux for 1 hour
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-99591f7569ee48f5910544eefcdcaaf3
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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