Toluene → Methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate

HRID 1012287Notes

Reaction equation

HRID 1012287 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:42]=[CH:41][C:18]3[C:19]4[N:23]([CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[C:22]2[CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=[CH:30][C:21]=2[C:20]=4[CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:9]1)=O)(C)(C)C.C1(C)C=CC=CC=1>FC(F)(F)C(O)=O>[CH:35]1([C:20]2[C:21]3[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][C:22]=3[N:23]3[C:19]=2[C:18]2[CH:41]=[CH:42][C:15]([O:14][CH:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)=[CH:16][C:17]=2[O:26][CH2:25][CH2:24]3)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

4

Reactant 2

HCID 1140TolueneHCID 23152338HCID 23152338, compound

Product 1

HCID 23152885Methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylateYield 28.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 3-(1-tert-butoxycarbonylpiperidin-3-yloxy)-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.68 g) was dissolved in trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature for 3 hr. Toluene was added to the reaction mixture and the solvent was evaporated under reduced pressure. 4N HCl-ethyl acetate solution (2.0 ml) was added to the obtained residue and the mixture was stirred, and the solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol=9:1) to give methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.16 g, yield 17%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. addition4N HCl-ethyl acetate solution (2.0 ml) was added to the obtained residue
  3. stirringthe mixture was stirred
  4. customthe solvent was evaporated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-b8abbe7220c541a8b27e8b5a2c2f8e20
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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