Potassium Hydroxide → 1-(2-Pyridinyl)-4-[4-(3-pyridinyl)butyl]piperazine

HRID 1534359Notes

Reaction equation

HRID 1534359 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[CH:2]=1.O.NN.[OH-].[K+]>C(O)CO.O>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 199096501-(3-Pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone

Product 1

HCID 199096411-(2-Pyridinyl)-4-[4-(3-pyridinyl)butyl]piperazineYield 40.2%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone (Example 2) (5.2 g, 0.0168 mol), hydrazine hydrate (1.9 g, 0.0603 mol), and potassium hydroxide (3 g, 0.0538 mol) in ethylene glycol (100 mL) is refluxed 12 hours removing the water formed with a Dean-Stark trap. The cooled reaction mixture is diluted with water (100 mL) and extracted with dichloromethane. The organic layer is dried (sodium sulfate) and the solvent evaporate in vacuo. The resulting residue is crystallized from 2-propanol and diethyl ether to give 2 g of 1-(2-pyridinyl)-4-[4-(3-pyridinyl)butyl]piperazine as a white solid; mp 54-64° C.

Workup

  1. customremoving the water
  2. customformed with a Dean-Stark trap
  3. customThe cooled reaction mixture
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer is dried (sodium sulfate)
  6. customthe solvent evaporate in vacuo
  7. customThe resulting residue is crystallized from 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-d5a79e601d9949aeab817710b01a2017
Source dataset
uspto-grants-1992_02
Patent number
US05089497

Reaction notes

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