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Triethylamine → N-(6-Methoxy-4-methyl-8-quinolinyl)-2,6-dimethyl-4-morpholinehexanamide

HRID 542854
Notes
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Reaction equation

HRID 542854 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][CH:24]1[O:29][CH:28]([CH3:30])[CH2:27][NH: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:26]3[CH2:25][CH:24]([CH3:23])[O:29][CH:28]([CH3:30])[CH2:27]3)[CH:11]=1)[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 1108622,6-Dimethylmorpholine2×HCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

Product 1

HCID 13853362N-(6-Methoxy-4-methyl-8-quinolinyl)-2,6-dimethyl-4-morpholinehexanamideYield 55.1%

Reagents, catalysts & solvents 1

HCID 241Benzene
Solvent
2×

Procedure

A mixture of 5.5 g (0.015 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide and 1.85 ml (0.018 mole) of 2,6-dimethylmorpholine in 90 ml of benzene was heated under reflux for 24 hr. Triethylamine (2 ml) was added and the mixture was heated under reflux for an additional 2 hr, allowed to cool, and filtered. The filtrate was washed with water, dried and concentrated. TLC(silica gel--ethyl acetate) demonstrated a mixture of the unchanged bromo compound, Rf(silica--ethyl acetate)=0.63, and the product, Rf=0.08. A solution of the residue, 1.3 ml (0.01 mole) of 2,6-dimethylmorpholine, and 1.5 ml of triethylamine in 80 ml of benzene was heated under reflux for 40 hr, allowed to cool, filtered, washed with water, dried and concentrated. The residue was chromatographed over 200 g of silica gel with 1 liter each of the following solutions of methanol in ethyl acetate: 1.5%, 2%, 3% to afford 3.7 g of crude product. Recrystallization from hexane afforded 3.3 g of the title compound, mp 87°-90°. The NMR spectrum confirmed the presence of hexane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for an additional 2 hr
  5. temperatureto cool
  6. filtrationfiltered
  7. washThe filtrate was washed with water
  8. customdried
  9. concentrationconcentrated
  10. additiona mixture of the unchanged bromo compound, Rf(silica--ethyl acetate)=0.63
  11. temperatureunder reflux for 40 hr
  12. temperatureto cool
  13. filtrationfiltered
  14. washwashed with water
  15. customdried
  16. concentrationconcentrated
  17. customThe residue was chromatographed over 200 g of silica gel with 1 liter each of the following solutions of methanol in ethyl acetate
  18. custom1.5%, 2%, 3% to afford 3.7 g of crude product
  19. customRecrystallization from hexane

Sources & evidence

ORD record
ord-861a705abb484b67992aaa5135c24890
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04659708

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes