Vinyl chloroformate → 8-(1-piperazinyl)Quinoline

HRID 992038Notes

Reaction equation

HRID 992038 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC=C)=O>C(Cl)Cl>[N:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 184140838-(4-Benzyl-piperazin-1-yl)quinoline

Product 1

HCID 118307868-(1-piperazinyl)QuinolineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(4-benzyl-piperazin-1-yl)quinoline (2.63 g, 8.7 mmol) in methylene chloride (30 ml) was added vinyl chloroformate (1.1 ml, 13 mmol) at room temperature slowly. The reaction mixture was refluxed for 2 hours, and then concentrated under vacuum. The residue was dissolved in 12 N hydrochloric acid (20 ml) and stirred at room temperature for 1 hour. The mixture was concentrated, the residue was taken up with 40 ml ethanol and heated up to 50° C. for 2 hours. The solvent was removed under vacuum, the residue was dissolved in 1 N sodium hydroxide-ethyl acetate and extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under vacuum. Chromatography (10-30% methanol-methylene chloride plus ammonium hydroxide) afforded 1.86 g (90%) yellow oil; MS EI m/e 213 (M)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in 12 N hydrochloric acid (20 ml)
  4. concentrationThe mixture was concentrated
  5. temperatureheated up to 50° C. for 2 hours
  6. customThe solvent was removed under vacuum
  7. dissolutionthe residue was dissolved in 1 N sodium hydroxide-ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washwashed with water
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-25bd9ef33fa840d7b3213d046e6ec165
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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