1-Chloroethyl chloroformate → HCID 86686045, compound

HRID 239138Notes

Reaction equation

HRID 239138 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:15]1[CH2:20][CH:19]=[C:18]([C:21]2[O:22][C:23]([CH3:26])=[CH:24][N:25]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1>ClCCl>[ClH:1].[CH3:26][C:23]1[O:22][C:21]([C:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=2)=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 86686043HCID 86686043, compound

Product 1

HCID 86686045HCID 86686045, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g 1-chloroethyl chloroformate was added to 24 g 1-benzyl-4-(5-methyl-oxazol-2-yl)-1,2,3,6-tetrahydro-pyridine in 200 mL dichlormethane at 0° C. under nitrogen. After 2 h the solution was concentrated and 200 mL methanol was added. The mixture was refluxed 4 h and concentrated. The residue was crystallized from dichlormethane to give 16 g of the desired product. Rf: 0.02 (petrolether/ethyl acetate=1/1), (M+H)+: 165

Workup

  1. concentrationAfter 2 h the solution was concentrated
  2. addition200 mL methanol was added
  3. temperatureThe mixture was refluxed 4 h
  4. concentrationconcentrated
  5. customThe residue was crystallized from dichlormethane

Sources & evidence

ORD record
ord-90e4619c91864a4eafd97df12fcaad26
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

Loading…