1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 21186685, compound

HRID 1384279Notes

Reaction equation

HRID 1384279 reaction equation
Cl[CH:2]1[C:8]2=[N:9][C:10]([CH3:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:7]2[CH2:6][CH2:5][CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH3:18][C:10]1[N:9]=[C:8]2[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][C:7]2=[CH:12][C:11]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21186666HCID 21186666, compound

Product 1

HCID 21186685HCID 21186685, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In an atmosphere of argon, ethyl 9-chloro-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (3.35 g, 12.5 mmol) was dissolved in toluene (12.0 ml), and the solution was mixed with 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (2.9 ml, 18.9 mmol) at 0° C. and then heated under reflux for 23 hours. The solvent was evaporated under reduced pressure, and the thus obtained residue was dissolved in ethyl acetate, mixed with water and then extracted with ethyl acetate. The thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:2) to obtain the title compound (2.82 g, 97.5%) as pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 23 hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe thus obtained residue was dissolved in ethyl acetate
  5. additionmixed with water
  6. extractionextracted with ethyl acetate
  7. washThe thus obtained organic layer was washed with water and saturated brine in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:2)

Sources & evidence

ORD record
ord-3f74638ead204489a023eb9bf2433257
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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