Thionyl Chloride → HCID 22318640, compound

HRID 497321Notes

Reaction equation

HRID 497321 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)O)[CH2:9][CH2:8]1)=[O:6])[CH3:3].S(Cl)([Cl:25])=O>C1C=CC=CC=1>[ClH:25].[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([Cl:1])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22318674HCID 22318674, compound

Product 1

HCID 22318640HCID 22318640, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

To 8.3 g of 1-ethoxycarbonyl-4-[2-(4-fluorophenyl)-2-hydroxyethyl]piperazine hydrochloride were added 20 ml of benzene and 2.5 ml of thionyl chloride, followed by heating at 50° C. for 10 minutes. The reaction solution was concentrated under reduced pressure, 25% aqueous ammonia solution and water were poured, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and, after removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. To the residue was poured 50 ml of 4M hydrogen chloride/ethyl acetate solution, the solution was concentrated under reduced pressure, and the resulting solid was washed with ether to give 8.1 g of 1-ethoxycarbonyl-4-[2-chloro-2-(4-fluorophenyl)ethyl]-piperazine hydrochloride.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, 25% aqueous ammonia solution and water
  2. additionwere poured
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customafter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo the residue was poured 50 ml of 4M hydrogen chloride/ethyl acetate solution
  9. concentrationthe solution was concentrated under reduced pressure
  10. washthe resulting solid was washed with ether

Sources & evidence

ORD record
ord-d97d323f9731431fbd2170ae5c977cbe
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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