Vinyl chloroformate → HCID 18414158, compound

HRID 992056Notes

Reaction equation

HRID 992056 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-71123e36daab478fbeaa4fbdac88b6ba
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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