Cyclohexylamine → HCID 19081700, compound

HRID 963405Notes

Reaction equation

HRID 963405 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8](=[CH:14][N:15]([CH3:17])C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4](Cl)[CH:3]=1.[CH:21]1(N)[CH2:26][CH2:25]C[CH2:23][CH2:22]1.CC([O-])(C)C.[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:15]2[CH:17]2[CH2:25][CH2:26][CH2:21][CH2:22][CH2:23]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 23665647Potassium tert-butoxideHCID 54513699HCID 54513699, compound

Product 1

HCID 19081700HCID 19081700, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

13ad) A solution of 20 g of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-dimethylaminoacrylate (Example 13ac)) in 200 ml of dimethyl sulphoxide is treated with 5.5 g of cyclohexylamine and stirred at room temperature under argon for 45 min. Immediately after the addition the solution begins to decolourize and a colourless, gel-like substance separates. 6.84 g of potassium tert-butylate are added in one portion to this suspension. The resulting suspension is stirred at room temperature for 10 min. and subsequently heated to 50° for 1.5 hrs. The reaction mixture is left to cool to room temperature, poured into 600 ml of ice-water and stirred for a further 30 min. The suspension is suction filtered, the filter residue is washed three times with 100 ml of water each time and three times with 100 ml of hexane each time and dried. Recrystallization of the crude product from ethyl acetate/hexane yields 14.8 g (90%) of ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 129°-133°.

Workup

  1. additionImmediately after the addition the solution
  2. stirringThe resulting suspension is stirred at room temperature for 10 min.
  3. temperaturesubsequently heated to 50° for 1.5 hrs
  4. waitThe reaction mixture is left
  5. temperatureto cool to room temperature
  6. stirringstirred for a further 30 min
  7. filtrationsuction filtered
  8. washthe filter residue is washed three times with 100 ml of water each time and three times with 100 ml of hexane each time
  9. customdried
  10. customRecrystallization of the crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e3114a59d32a499892bd161a09a15545
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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