1-Chloroethyl chloroformate → 1-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate

HRID 1394064Notes

Reaction equation

HRID 1394064 reaction equation
C[N:2]1[CH2:7][CH:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[C:14]([O:16][CH:17]([Cl:19])[CH3:18])=[O:15]>ClC(Cl)C>[N:2]1([C:14]([O:16][CH:17]([Cl:19])[CH3:18])=[O:15])[CH2:3][CH:4]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 566021Ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate

Product 1

HCID 692236561-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate (47 g, 278 mmol) in dichloroethane (800 mL) was treated with α-chloroethyl chloroformate (50 g, 350 mmol) dropwise at 0° C. The mixture was warmed to room temperature, refluxed for 2 hours, and then allowed to cool to room temperature. The mixture was concentrated under reduced pressure and the residue was purified via column chromatography (SiO2, ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 6.88 (m, 1H), 6.61 (q, 1H), 4.22 (q, 2H), 4.16 (m, 2H), 7.35 (d, 2H), 3.58 (m, 2H), 2.44 (m, 2H), 1.82 (d, 3H), 1.30 (t, 3H).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureto cool to room temperature
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified via column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-512b60c1c43243d791bc4a88bfaba741
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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