Triethylamine → 6-[(6-Methoxy-4-methyl-8-quinolinyl)amino]-1-hexanol

HRID 542828Notes

Reaction equation

HRID 542828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:14].Cl[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].C(N(CC)CC)C.ClC(O)CCCCC>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:14]

Participants

6

Reactant 4

HCID 8471Triethylamine3×HCID 748286-Chloro-1-hexanolHCID 6047536-Methoxy-4-methyl-8-quinolinamineHCID 12768704Chlorohexanol2×

Product 1

HCID 130775316-[(6-Methoxy-4-methyl-8-quinolinyl)amino]-1-hexanolYield 55.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 1.9 g (0.01 mole) of 6-methoxy-4-methyl-8-quinolinamine and 1.4 g (0.01 mole) of 6-chlorohexanol at 150° was added portionwise over one hr 1.4 ml (0.01 mole) of triethylamine. The mixture was stirred for 1 hr at the same temperature, and then 0.8 g (0.0056 mole) of 1-chlorohexanol was added, followed by the portionwise addition of 0.8 (0.0056 mole) of triethylamine. The mixture was stirred for 1 hr and the procedure was repeated with 0.5 g (0.0037 mole) of 1-chlorohexanol and 0.5 ml of triethylamine. After the mixture was stirred an additional hr, the mixture was allowed to cool, diluted with acetone, filtered, and concentrated to dryness in vacuo. The residue was dissolved in dichloromethane and chromatographed over 70 g of silica gel first with 500 ml of dichloromethane and then with the following solutions of ethyl acetate in dichloromethane: 5% (500 ml), 10% (1 liter), 15% (500 ml), and finally 20% (500 ml). Fractions of the 20% eluant containing the product, Rf(silica--ethyl acetate)=0.3, were combined and concentrated to dryness in vacuo. Recrystallization from 2-propanol afforded 1.6 g (55%) of the title compound, mp 97°-99°.

Workup

  1. stirringThe mixture was stirred for 1 hr
  2. stirringAfter the mixture was stirred an additional hr
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated to dryness in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane
  7. customchromatographed over 70 g of silica gel first with 500 ml of dichloromethane
  8. additionFractions of the 20% eluant containing the product, Rf(silica--ethyl acetate)=0.3
  9. concentrationconcentrated to dryness in vacuo
  10. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-36d900ce57a04747b519e497255e2464
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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