Piperazine → 1-(2-Methylpyridin-4-yl)piperazine

HRID 2232397Notes

Reaction equation

HRID 2232397 reaction equation
[N+]([O-])(O)=O.Cl[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[CH:7]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+].C(O)CCCC>O>[CH3:12][C:8]1[CH:7]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 62761-PentanolHCID 516892Sodium BicarbonateHCID 678656864-Chloro-2-methylpyridine nitrate

Product 1

HCID 167623771-(2-Methylpyridin-4-yl)piperazineYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-2-methylpyridine nitrate (5.00 g), piperazine (9.00 g), anhydrous sodium bicarbonate (6.60 g) and amyl alcohol (60 ml) was heated under reflux for 18 hours. The mixture was cooled and water was added to dissolve inorganic material. The organic layer was washed four times with brine and all the aqueous extracts were combined and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulphate and evaporated. The residue was crystallised from ethyl acetate/hexane to give 1-(2-methylpyrid-4-yl)piperazine (2.80 g), m.p. 93°-94° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. dissolutionto dissolve inorganic material
  5. washThe organic layer was washed four times with brine and all the aqueous extracts
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customThe residue was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bacd9710458a40828c4143183fc73e44
Source dataset
uspto-grants-1988_11
Patent number
US04788196

Reaction notes

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