Piperazine → HCID 57059596, compound

HRID 1655202Notes

Reaction equation

HRID 1655202 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18](Cl)=[N:17][CH:16]=1.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[N:17][CH:16]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 19791100HCID 19791100, compound

Product 1

HCID 57059596HCID 57059596, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.36 g of N-(11-hydroxy-1-undecanyl)-6-chloronicotinamide and 3.15 g of piperazine were suspended in 50 ml of toluene and the suspension was stirred at 120°-130° C. for 5 hrs. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (chloroform:methanol=5:1) to obtain quantitatively N-(11-hydroxy-1-undecanyl)-6-piperazinylnicotinamide. This compound was added under ice-cooling to 10 ml of fuming nitric acid and the mixture was stirred below 5° C. for 4 hrs. This reaction mixture was poured into an aqueous sodium hydrogencarbonate, extracted with methylene chloride, washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=5:1) and recrystallized from chloroform/hexane to give 0.5 g (15%) of the title compound.

Workup

  1. concentrationThis reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-c0688ec1394d4e2bb9a9ffef08b2766b
Source dataset
uspto-grants-1993_10
Patent number
US05250526

Reaction notes

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