Piperazine → N-(6-Methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide

HRID 542848Notes

Reaction equation

HRID 542848 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20])=[O:8].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O>[CH3:22][O:21][C:12]1[CH:13]=[C:14]2[C:19](=[C:10]([NH:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:11]=1)[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

Product 1

HCID 13853361N-(6-Methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamideYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 g (0.022 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)-hexanamide and 35 g (0.41 mole) of piperazine was stirred at 125° for 1 hr, cooled and suspended in water. The resulting fine precipitate was collected and dissolved in dichloromethane. The solution was washed with water, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 560 g of alumina with 500 ml each of the following solutions of methanol in an ethyl acetate:dichloromethane (1:9) mixture: 2%, 3%, 4%, 5% and 10% to afford 2.6 g of crude product, Rf(alumina--75 parts of ethyl acetate:25 parts of methanol:1 part of triethylamine)=0.38. Recrystallization from toluene afforded 1.9 g (23%) of the title compound, mp 122°-124°.

Workup

  1. temperaturecooled
  2. customThe resulting fine precipitate was collected
  3. dissolutiondissolved in dichloromethane
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated to dryness in vacuo
  7. customThe residue was chromatographed over 560 g of alumina with 500 ml each of the following solutions of methanol in an ethyl acetate:dichloromethane (1:9) mixture
  8. custom2%, 3%, 4%, 5% and 10% to afford 2.6 g of crude product, Rf(alumina--75 parts of ethyl acetate:25 parts of methanol:1 part of triethylamine)=0.38
  9. customRecrystallization from toluene

Sources & evidence

ORD record
ord-2473eee81ea0457ea0e9068df144b2b2
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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