2-Chloroethyl chloroformate → HCID 22277841, compound

HRID 1064028Notes

Reaction equation

HRID 1064028 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11][CH2:10]2)[C:5]([F:22])=[C:4]([F:23])[N:3]=1.[Cl:24]C(OCCCl)=O>ClCCCl>[ClH:24].[F:23][C:4]1[C:5]([F:22])=[C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:7]([F:8])=[C:2]([F:1])[N:3]=1

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 22277827HCID 22277827, compound

Product 1

HCID 22277841HCID 22277841, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To an ice bath cooled, stirred solution of 1-(2,3,5,6-tetrafluoropyridin-4-yl)-4-benzylpiperazine (Method 20; 4.59 g, 14.1 mmol) in 1,2-dichloroethane (40 ml) was added chloroethyl chloroformate (1.6 ml, 14.7 mmol) over five minutes. The solution was heated to reflux and stirred for two hours and allowed to cool to ambient temperature. Volatile material was removed by evaporation. The residue was dissolved in methanol, heated to reflux and stirred for 2.5 hours, allowed to cool to ambient temperature. Volatile material was removed by evaporation. The residue was purified by chromatography eluting with 5-10% MeOH in DCM to give a solid which was triturated with ether to give the title compound (2.57 g) as a solid. NMR 3.05 (m, 4H), 3.53 (m, 4H); m/z 236.

Workup

  1. temperatureTo an ice bath cooled
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. customVolatile material was removed by evaporation
  5. dissolutionThe residue was dissolved in methanol
  6. temperatureheated
  7. temperatureto reflux
  8. stirringstirred for 2.5 hours
  9. temperatureto cool to ambient temperature
  10. customVolatile material was removed by evaporation
  11. customThe residue was purified by chromatography
  12. washeluting with 5-10% MeOH in DCM
  13. customto give a solid which
  14. customwas triturated with ether

Sources & evidence

ORD record
ord-1b9cb76e4170495cb2511d643a9d12de
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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