Potassium Hydroxide → 1-(3-Methoxypyridin-4-yl)piperazine

HRID 1647807Notes

Reaction equation

HRID 1647807 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][N:12](C(OC)=O)[CH2:11][CH2:10]1.O.NN.[OH-].[K+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 19921673HCID 19921673, compound

Product 1

HCID 152883081-(3-Methoxypyridin-4-yl)piperazineYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4-(3-methoxy-4-pyridinyl)-1-piperazinecarboxylate (1.2 g, 4.7 mmol) in 50 mL of EtOH containing 1 mL of 85% hydrazine hydrate and potassium hydroxide (12 g, 210 mol) was heated to reflux for 12 h. The reaction mixture was cooled, concentrated in vacuo and the residue dissolved in EtOAc. The organic extracts were dried (brine, MgSO4), filtered and concentrated in vacuo. Silica gel chromatography (3:1:0.01 CH2Cl2 -MeOH-Et3N) of the residue gave the desired compound (0.42 g, 46%).

Workup

  1. temperatureto reflux for 12 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in EtOAc
  5. dry with materialThe organic extracts were dried (brine, MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e1d0d80f6a74c48af972070498aaf79
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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