Vinyl chloroformate → HCID 18414146, compound

HRID 428530Notes

Reaction equation

HRID 428530 reaction equation
C(N1CCN([C:14]2[CH:23]=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)CC1)C1C=CC=CC=1.ClC(O[CH:28]=[CH2:29])=O>>[N:15]1([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[N:22]=[CH:23][CH:14]=[N:15]3)[CH2:29][CH2:28][NH:22][CH2:23][CH2:14]1

Participants

3

Reactant 2

HCID 78808Vinyl chloroformateHCID 45517562-[4-(Phenylmethyl)-1-piperazinyl]quinoxaline

Product 1

HCID 18414146HCID 18414146, compoundYield 127.3%

Procedure

To a room temperature solution of 1-benzyl-4-(quinoxalin-yl)-piperazine (1.0 g, 3.3 mmol) in anhydrous CH2C2 under nitrogen was added vinyl chloroformate (0.34 mL, 3.9 mmol) drop wise. The reaction mixture was heated at reflux 2 hours. The reaction was cooled, concentrated to dryness and concentrated HCl (25 mL) and 1,4-dioxane (25 mL) were added. The resulting solution was stirred at ambient temperature overnight. The solution was basified with 2.5 N NaOH (300 mL) and extracted into EtOAc (3×200 mL). The organic layers were combined, dried over Na2SO4, concentrated and chromatographed (10% MeOH/CH2Cl2/NH4OH) to give 450 mg (64%) of an orange solid: mp 106-108° C.: MS (+) ESI m/e 215 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux 2 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated to dryness and concentrated HCl (25 mL) and 1,4-dioxane (25 mL)
  5. additionwere added
  6. extractionextracted into EtOAc (3×200 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customchromatographed (10% MeOH/CH2Cl2/NH4OH)

Sources & evidence

ORD record
ord-18456b6cb55345e48f1f69a3a556730a
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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