Vinyl chloroformate → HCID 18414158, compound

HRID 428535Notes

Reaction equation

HRID 428535 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([O:25][CH3:26])[CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[C:19]3[CH3:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC=C)=O>C(Cl)Cl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]2[C:23](=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:15]=1)[N:22]=[CH:21][CH:20]=[C:19]2[CH3:24]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 18414092HCID 18414092, compound

Product 1

HCID 18414158HCID 18414158, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-benzyl-4-(6-methoxy-4-methylquinolin-8-yl)piperazine (2.0 g, 5.76 mmol), methylene chloride (50 mL) and vinyl chloroformate (0.8 mL, 8.64 mmol) were refluxed for 4 hours. The mixture was concentrated, then dissolved in a 1:1 mixture of dioxane/conc. HCl and stirred at ambient temperature for 18 hours. The reaction mixture was made basic with 2.5 N aqueous NaOH and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), then were dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.6 g (47%) of the title compound: mp 208-209° C.

Workup

  1. temperaturewere refluxed for 4 hours
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in a 1:1 mixture of dioxane/conc
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
  6. dry with materialwere dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7ee250198f314306bd350fe43390a8f4
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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