Water → 1-(6-Methoxypyridin-3-YL)piperazine

HRID 266064Notes

Reaction equation

HRID 266064 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl.Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+].O>CC(O)CC>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 811216-Methoxy-3-pyridinylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 190323961-(6-Methoxypyridin-3-YL)piperazineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 6-methoxy-3-pyridinamine (0.2 mol) and 2-chloro-N-(2-chloroethyl)-ethanamine hydrochloride (0.3 mol) in 2-butanol (500 ml) was stirred and refluxed. Potassium carbonate (0.7 mol) was added portionwise (20 g/h), the mixture was refluxed for 48 hours, an additional amount of potassium carbonate (30 g) was added and the mixture was stirred for 48 hours. The mixture was poured into water, extracted with CH2Cl2 and separated. The organic layer was dried, filtered and evaporated, yielding 38 g (98%) of 1-(6-methoxy-3-pyridinyl)piperazine (interm. 29).

Workup

  1. temperaturerefluxed
  2. temperaturethe mixture was refluxed for 48 hours
  3. stirringthe mixture was stirred for 48 hours
  4. extractionextracted with CH2Cl2
  5. customseparated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e01e1b8a9e3c495989d14e003f27f811
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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