1-Chloroethyl chloroformate → HCID 19391664, compound

HRID 217467Notes

Reaction equation

HRID 217467 reaction equation
C[N:2]1[CH2:7][CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.ClC(OC(Cl)=O)C>ClC(Cl)C>[NH:2]1[CH2:3][CH:4]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 12674336HCID 12674336, compound

Product 1

HCID 19391664HCID 19391664, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of ethyl (1-methyl-1,2,3,6-tetrahydropyridin-4-yl)acetate (2.05 g) in dichloroethane (14 mL) was added 1-chloroethyl-chloroformate (1.5 mL) at 0° C. The reaction liquid was heated and refluxed for 2.5 hours, and then concentrated under reduced pressure. The residue was dissolved in MeOH (14 mL), and heated and refluxed for 1 hour. After concentration under reduced pressure, the residue was purified by amino column chromatography (chloroform:methanol=100:0 to 80:20) to obtain ethyl 1,2,3,6-tetrahydropyridin-4-ylacetate (130 mg) as a brown liquid.

Workup

  1. customThe reaction liquid
  2. temperaturewas heated
  3. temperaturerefluxed for 2.5 hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in MeOH (14 mL)
  6. temperatureheated
  7. temperaturerefluxed for 1 hour
  8. concentrationAfter concentration under reduced pressure
  9. customthe residue was purified by amino column chromatography (chloroform:methanol=100:0 to 80:20)

Sources & evidence

ORD record
ord-c8b9c99d0aa7475bb775bb1ae24e2d55
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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