Hydrochloric Acid → 2-(4-Chlorophenyl)-3-(piperazin-1-yl)pyrazine

HRID 220424Notes

Reaction equation

HRID 220424 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68736815HCID 68736815, compound

Product 1

HCID 685942572-(4-Chlorophenyl)-3-(piperazin-1-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3′-(4-chloro-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester in DCM (10 mL), add 4 M aqueous HCl (5 equiv) and stir for 2 hr. at ambient temperature. Concentrate under reduced pressure, dissolve in methanol (2 mL) and purify by SCX, eluting the product from the ion-exchange resin using 2 M NH3 in methanol, to give the title preparation (0.103 g, 100%). MS (ES): m/z=259 [M+H]+.

Workup

  1. customat ambient temperature
  2. concentrationConcentrate under reduced pressure
  3. dissolutiondissolve in methanol (2 mL)
  4. custompurify by SCX
  5. washeluting the product from the ion-exchange resin
  6. customto give the title
  7. custompreparation (0.103 g, 100%)

Sources & evidence

ORD record
ord-98e9829cba0b4dfe94b1c6dfc18f2409
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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