Potassium Iodide → HCID 19909642, compound

HRID 1534357Notes

Reaction equation

HRID 1534357 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7]CCCl.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[I-].[K+].[CH3:25][N:26]([CH3:29])C=O>>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:18][CH2:19][N:20]([CH2:6][CH2:5][CH2:4][C:3]2[CH:25]=[N:26][CH:29]=[CH:7][CH:2]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 944591-(2-Pyridyl)piperazineHCID 179113Pyridine, chloropropyl-

Product 1

HCID 19909642HCID 19909642, compound

Conditions

Temperature
80 °C

Procedure

A solution of 3-pyridinylpropylchloride (Example A) (3.0 g, 0.0193 mol), 1-(2-pyridinyl)piperazine (3.15 g, 0.0193 mol), potassium iodide (0.8 g, 0.005 mol) is dissolved in N,N-dimethylformamide (80 mL) and heated to 80° C. for 12 hours. The reaction is cooled and the precipitate is filtered. The filtrate is washed with sodium carbonate and extracted with dichloromethane. The organic layer is evaporated in vacuo and the residue is purified by column chromatography (silica gel, 10% ethanol/ethyl acetate). The major product is taken up in diethyl ether and the precipitate is filtered. The filtrate is evaporated in vacuo to give 0.8 g of 1-(2-pyridinyl)-4-[3-(3-pyridinyl)propyl]piperazine as a white solid; mp 51-52° C.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationthe precipitate is filtered
  3. washThe filtrate is washed with sodium carbonate
  4. extractionextracted with dichloromethane
  5. customThe organic layer is evaporated in vacuo
  6. customthe residue is purified by column chromatography (silica gel, 10% ethanol/ethyl acetate)
  7. filtrationthe precipitate is filtered
  8. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-53641a4cb697449b885deb709e573bca
Source dataset
uspto-grants-1992_02
Patent number
US05089497

Reaction notes

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