1,2-Dichloroethane → HCID 22277841, compound

HRID 2055334Notes

Reaction equation

HRID 2055334 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]CCCl>>[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

3

Reactant 2

HCID 111,2-DichloroethaneHCID 22277827HCID 22277827, compound

Product 1

HCID 22277841HCID 22277841, compound

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 chloroforinate (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 refiux 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. additionwas added chloroethyl chloroforinate (1.6 ml, 14.7 mmol) over five minutes
  3. temperatureThe solution was heated
  4. temperatureto reflux
  5. customVolatile material was removed by evaporation
  6. dissolutionThe residue was dissolved in methanol
  7. temperatureheated to refiux
  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-ca11d6a5dc554785866cc76716c89975
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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