1-Chloroethyl chloroformate → HCID 21955172, compound

HRID 2213050Notes

Reaction equation

HRID 2213050 reaction equation
ClC(OC(Cl)=O)C.C1(C[N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=3)[C:17](=[O:28])[CH2:16]2)C=CC=CC=1>ClCCl>[Cl:27][C:23]1[N:22]=[C:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][C:17]2=[O:28])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 21955204HCID 21955204, compound

Product 1

HCID 21955172HCID 21955172, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-14 °C

Procedure

1-Chloroethylchloroformate (143 μL, 1.33 mmol) was added slowly to a stirred, cooled (−18° C.) solution of 4-phenylmethyl-1-(6-chloro-2-pyridinyl)piperazin-2-one (Description 152, 400 mg, 1.33 mmol) in dichloromethane (10 mL) and the mixture was stirred at −14° C. for 3 hours. The solvent was evaporated under reduced pressure, methanol (10 mL) was added and the mixture was heated under reflux for 30 minutes. The mixture was cooled, the solvent was evaporated under reduced pressure and methanolic ammonia (2M, 10 mL) was added. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (120:8:1), to give the title compound as a tan gum (118 mg, 42%). m/z (ES+) 212, 214 (M+1)+.

Workup

  1. customThe solvent was evaporated under reduced pressure, methanol (10 mL)
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. temperatureThe mixture was cooled
  6. customthe solvent was evaporated under reduced pressure and methanolic ammonia (2M, 10 mL)
  7. additionwas added
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by flash column chromatography on silica gel
  10. washeluting with CH2Cl2/MeOH/NH3(Aq.) (120:8:1)

Sources & evidence

ORD record
ord-a8a5df72ee7d45039d606bd1e2bdffb4
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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