Potassium Iodide → 1-(3-Pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone

HRID 1534358Notes

Reaction equation

HRID 1534358 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[I-].[K+]>C(Cl)(Cl)Cl>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:22]2[CH2:23][CH2:24][N:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)[CH2:20][CH2:21]2)[CH:8]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 944591-(2-Pyridyl)piperazineHCID 124710054-Chloro-1-(pyridin-3-YL)butan-1-one

Product 1

HCID 199096501-(3-Pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanoneYield 44.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-chloro-1-(3-pyridinyl)-1-butanone (Example B) (9 g, 0.049 mol), 1-(2-pyridinyl)piperazine (24 g, 0.147 mol), and potassium iodide (0.8 g, 0.005 mol) is heated to 120° C. for 5 minutes. The residue is taken up in chloroform (40 mL) and the precipitate is filtered. The filtrate is evaporated in vacuo and purified by column chromatography (silica gel, 2% methanol/dichloromethane). The major product is crystallized from 2-propanol/diethyl ether to give 6.7 g 1-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone as a white solid; mp 89° C.

Workup

  1. filtrationthe precipitate is filtered
  2. customThe filtrate is evaporated in vacuo
  3. custompurified by column chromatography (silica gel, 2% methanol/dichloromethane)
  4. customThe major product is crystallized from 2-propanol/diethyl ether

Sources & evidence

ORD record
ord-71340c46f9db4fc39852afb8f05d68a4
Source dataset
uspto-grants-1992_02
Patent number
US05089497

Reaction notes

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