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

HRID 542831Notes

Reaction equation

HRID 542831 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].[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>C1C=CC=CC=1>[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:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)[CH:11]=1)[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

Product 1

HCID 13077513N-(6-Methoxy-4-methyl-8-quinolinyl)-4-methyl-1-piperazinehexanamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.5 g (0.015 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide and 1.8 g (0.018 mole) of N-methylpiperazine in 70 ml of benzene was heated under reflux for 20 hr, treated with 2 ml of triethylamine, and heated for an additional 24 hr. The mixture was allowed to cool, filtered and the filtrate was washed with water, dried and concentrated to dryness in vacuo. The residue was recrystallized twice from n-hexane containing a little toluene and then dried in vacuo at 68° to afford 3.1 g (53%) of the title compound, mp 104°-107°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hr
  3. temperatureheated for an additional 24 hr
  4. temperatureto cool
  5. filtrationfiltered
  6. washthe filtrate was washed with water
  7. customdried
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue was recrystallized twice from n-hexane containing a little toluene
  10. customdried in vacuo at 68°

Sources & evidence

ORD record
ord-15a34611a2e3437ba1064a2cab86f505
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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