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Potassium Carbonate → 2-[4-[4-(3-Chlorophenyl)piperazin-1-yl]butyl]-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one

HRID 358222
Notes
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Reaction equation

HRID 358222 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+].[N:27]1[NH:28][C:29](=[O:36])[N:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=12.[Na]>C(Cl)(Cl)Cl.C1(C)C(C)=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][N:28]3[C:29](=[O:36])[N:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]4=[N:27]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 256811-(3-Chlorophenyl)piperazine monohydrochlorideHCID 813641-Bromo-4-chlorobutaneHCID 70507128Sodium 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 133747472-[4-[4-(3-Chlorophenyl)piperazin-1-yl]butyl]-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-oneYield 43%

Reagents, catalysts & solvents

2
HCID 6212ChloroformSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 8.0 g. (0.0343 mole) of 1-(3-chlorophenyl)piperazine hydrocloride, 5.88 g. (0.0343 mole) of 1-bromo-4-chlorobutane, 9.48 g. (0.9686 mole) of finely powdered potassium carbonate, and 200 ml. of dry xylene was refluxed for 22 hr. To this mixture there was then added 5.39 g. (0.0343 mole) of sodium 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one, and the resulting suspension was refluxed an additional 72 hr. The mixture was then cooled, diluted with 200 ml. of chloroform, stirred for 15 min. and filtered. The clear filtrate was concentrated to an oil (9.8 g.) under reduced pressure. The residue was recrystallized from ET2O--EtOH--CHCl3 to afford 2.31 g. (43%) of the desired product, m.p. 122°-123°.

Workup

  1. additionA mixture of 8.0 g
  2. additionTo this mixture there was then added 5.39 g
  3. temperatureThe mixture was then cooled
  4. additiondiluted with 200 ml
  5. filtrationfiltered
  6. concentrationThe clear filtrate was concentrated to an oil (9.8 g.) under reduced pressure
  7. customThe residue was recrystallized from ET2O
  8. customEtOH--CHCl3 to afford 2.31 g

Sources & evidence

ORD record
ord-9921cd8d05fa42deba4b5fc11d0e9396
Source dataset
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04465683

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes