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Toluene → 1-(2,6-Dimethoxy-4-pyridyl)piperazine

HRID 333955
Notes
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Reaction equation

HRID 333955 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](Cl)[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 4837PiperazineHCID 123244194-Chloro-2,6-dimethoxypyridine

Product 1

HCID 668358261-(2,6-Dimethoxy-4-pyridyl)piperazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.5 g (13 mmol) 2,6-dimethoxy-4-chloro-pyridine and 6.21 g (65 mmol) piperazine were heated at reflux in 22 ml anhydrous pyridine for 20 hours. After cooling (precipitation was detected) 50 ml of toluene was added and the suspension was filtered. The filtrate was concentrated under reduced pressure, piperazine and pyridine were azeotropically removed by repeated evaporation with toluene (five times). The residue was triturated with diethylether/petrolether (1:1) and dried in vacuo. The product was obtained as yellow solid and used directly in the next step.

Workup

  1. additionwas added
  2. filtrationthe suspension was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure, piperazine and pyridine
  4. customwere azeotropically removed
  5. customevaporation with toluene (five times)
  6. customThe residue was triturated with diethylether/petrolether (1:1)
  7. customdried in vacuo
  8. customThe product was obtained as yellow solid

Sources & evidence

ORD record
ord-e9e29214697d4a22b51c7767628b2b4e
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883791B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes