Hydrochloric Acid → 6-Chloro2-(4-allyl-1-piperazinyl)-pyrazine hydrochloride

HRID 261067Notes

Reaction equation

HRID 261067 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[N:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23].Cl>C(#N)C.C(O)C.C(O)(C)C>[ClH:2].[Cl:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][N:12]([CH2:23][CH:22]=[CH2:21])[CH2:13][CH2:14]2)[CH:6]=[N:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 198421MK-212 hydrochloride

Product 1

HCID 203960116-Chloro2-(4-allyl-1-piperazinyl)-pyrazine hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22179027Isopropanol ethanolSolvent

Procedure

A stirred suspension of 6-chloro-2-(1-piperazinyl)-pyrazine hydrochloride (2.35 g, 10.0 mmol) and 2.8 g potassium carbonate in 25 ml of acetonitrile at 50° C. is treated with 0.9 ml (10.4 mmol) allylbromide. After 4 hours at 50° C. the mixture is concentrated under vacuum and the residue partitioned between water and chloroform. The chloroform extract is chromatographed on silica gel. Elution with 1% methanol-chloroform gives fractions containing 0.4 g (15%) title salt, mp 233.5°-234° C. by treatment with hydrogen chloride in ethanol-isopropanol.

Workup

  1. concentrationAfter 4 hours at 50° C. the mixture is concentrated under vacuum
  2. customthe residue partitioned between water and chloroform
  3. extractionThe chloroform extract
  4. customis chromatographed on silica gel
  5. washElution with 1% methanol-chloroform
  6. customgives fractions

Sources & evidence

ORD record
ord-b94f9e1f61b3411887e43579950b58a4
Source dataset
uspto-grants-1979_08
Patent number
US04163849

Reaction notes

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