1-Chloroethyl chloroformate → HCID 22718220, compound

HRID 1582764Notes

Reaction equation

HRID 1582764 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:16][CH3:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:15]([CH2:16][CH3:17])[CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22718328HCID 22718328, compound

Product 1

HCID 22718220HCID 22718220, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1-Benzyl-4-[2-(4-fluorophenoxy)butyl]piperazine 717 mg was dissolved in dichloroethane 10 ml, and 1-chloroethyl chloroformate 598 mg was added thereto, and the mixture was stirred for 2 hours under reflux with heating. After the reaction mixture was concentrated, methanol 10 ml was added thereto, and the mixture was stirred for 1 hour under reflux with heating. After the mixture was evaporated, it was partitioned by adding ether and 2N hydrochloric acid, and the aqueous layer was neutralized with 2N sodium hydroxide followed by extracting with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate anhydride and evaporated, whereby the title compound 168 mg, 32% was obtained as a colorless oil.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. concentrationAfter the reaction mixture was concentrated
  4. additionmethanol 10 ml was added
  5. stirringthe mixture was stirred for 1 hour
  6. temperatureunder reflux
  7. temperaturewith heating
  8. customAfter the mixture was evaporated
  9. customit was partitioned
  10. additionby adding ether and 2N hydrochloric acid
  11. extractionby extracting with ethyl acetate
  12. washThe organic layer was washed with water and brine successively
  13. dry with materialdried over magnesium sulfate anhydride
  14. customevaporated

Sources & evidence

ORD record
ord-d030076453014046943c4335f20219f6
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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