Piperidine → (1E,6E)-1-(1H-indol-6-yl)-7-[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dione

HRID 632503

Reaction equation

HRID 632503 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:8]=2)[CH:3]=[CH:2]1.[B]=O.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][O:28][C:29]2[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=2)[CH2:22][CH2:21]1.B(OCCCC)(OCCCC)OCCCC.N1CCCCC1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])/[CH:15]=[CH:33]/[C:32]3[CH:35]=[CH:36][C:29]([O:28][CH2:27][CH2:26][N:23]4[CH2:24][CH2:25][O:20][CH2:21][CH2:22]4)=[CH:30][CH:31]=3)[CH:8]=2)[CH:3]=[CH:2]1

Participants

9

Reactant 6

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 12712Tributyl borateHCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 6327189Boron monoxideHCID 67107107(E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione

Product 1

HCID 117888945(1E,6E)-1-(1H-indol-6-yl)-7-[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dioneYield 37.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 2.5 g of (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione were added 44 mL of AcOEt and 1.07 g of boron oxide, and the mixture was stirred at 70° C. for 40 minutes. To this, 2.27 g of 4-(2-morpholinoethoxy)benzaldehyde and 7.07 mL of tributyl borate were successively added, and the mixture was stirred at the same temperature for 40 minutes. Then, 0.11 mL of piperidine was added, and the mixture was stirred at 70° C. for 1.5 hours and was allowed to cool back to room temperature. To the reaction mixture, 22 mL of a 20% K2CO3 aqueous solution and 20 mL of THF were added and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated, washed with saturated brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/acetone or CHCl3/methanol system) to give 1.62 g of the title compound (33% yield).

Workup

  1. stirringthe mixture was stirred at the same temperature for 40 minutes
  2. stirringthe mixture was stirred at 70° C. for 1.5 hours
  3. temperatureto cool back to room temperature
  4. stirringthe mixture was stirred at room temperature for 10 minutes
  5. customThe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (CHCl3/acetone or CHCl3/methanol system)

Sources & evidence

ORD record
ord-a139d8c51116409e8c693eaad08f4589
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Linked notes

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