Piperazine → 3'-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 220427Notes

Reaction equation

HRID 220427 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(Cl)Cl>O>[Cl:15][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:3][CH:4]=[CH:5][N:6]=2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6344DichloromethaneHCID 656467322-Chloro-3-(3,4-dichloro-phenyl)-pyrazine

Product 1

HCID 685943053'-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 2-chloro-3-(3,4-dichloro-phenyl)-pyrazine (0.124 g, 0.477 mmol) and piperazine (1.40 gm; 16.3 mmol) and heat the mixture for 2 hr. at 120° C. Cool to room temperature, and add DCM (50 mL) and water (50 mL). Separate the layers and extract the aqueous layer with DCM (2×25 mL). Combine the organic layers, wash with brine, dry (MgSO4) and concentrate. Purify via chromatography on silica gel eluting 0-15% methanol in DCM to give the title preparation (0.118 gm, 80%). MS (ES+) m/z: 310 (M+H)+.

Workup

  1. customat 120° C
  2. customSeparate the layers
  3. extractionextract the aqueous layer with DCM (2×25 mL)
  4. washCombine the organic layers, wash with brine
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate
  7. customPurify via chromatography on silica gel eluting 0-15% methanol in DCM
  8. customto give the title
  9. custompreparation (0.118 gm, 80%)

Sources & evidence

ORD record
ord-ffbfb118e70041baa45433c584bc82e8
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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