Piperidine → HCID 76310264, compound

HRID 570636Notes

Reaction equation

HRID 570636 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH:13]=O)=[CH:10][C:9]([O:15][CH3:16])=[CH:8][CH:7]=2)([CH3:3])[CH3:2].[C:17]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)(=[O:19])[CH3:18].N1CCCCC1>CO>[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1/[CH:13]=[CH:18]/[C:17]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[O:19])=[CH:10][C:9]([O:15][CH3:16])=[CH:8][CH:7]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 142824-AcetylpyridineHCID 84682738HCID 84682738, compound

Product 1

HCID 76310264HCID 76310264, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

2-Isopropyl-5-methoxyindole-3-carboxaldehyde (105 mg, 0.48 mmol) was dissolved in anhydrous methanol (5 mL) under an atmosphere of Argon (g). 4-Acetylpyridine (87.2 mg, 0.72 mmol) and piperidine (61.3 mg, 0.72 mmol) were added to the reaction mixture and the solution was refluxed for 24 hours. A precipitate slowly formed which was collected, washed with cold MeOH (30 mL) and dried overnight in an oil driven vacuum pump equipped to a vacuum desiccator heated to 40° C. to yield a bright yellow powder (102 mg, 66%): TLC Rf 0.38 in 4:1 ethyl acetate/hexanes. Melting point=252-253° C. 1H NMR (600 MHz, d6-DMSO) δ 11.78 (s, 1H), 8.82-8.81 (m, 2H), 8.15-8.13 (d, 1H, J=15.24 Hz), 7.94 (m, 2H), 7.45 (d, 1H, J=2.28 Hz), 7.41-7.38 (d, 1H, J=15.18 Hz), 7.36-7.34 (d, 1H, J=8.7 Hz), 6.88-6.87 (dd, 1H, J1=2.34 Hz, J2=8.64 Hz), 3.87 (s, 3H), 3.54-3.49 (m, 1H), 1.35-1.34 (d, 6H, J=6.96 Hz); 13C NMR (150 MHz, d6-DMSO) δ 188.6, 155.7, 155.4, 151.1, 145.6, 139.6, 131.8, 126.6, 121.9, 113.5, 113.0, 111.6, 105.0, 104.4, 56.1, 26.0, 22.8. Elemental analysis calculated for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 74.78; H, 6.42; N, 8.68.

Workup

  1. temperaturethe solution was refluxed for 24 hours
  2. customA precipitate slowly formed which
  3. customwas collected
  4. washwashed with cold MeOH (30 mL)
  5. customdried overnight in an oil
  6. customequipped to a vacuum desiccator

Sources & evidence

ORD record
ord-6899e84e35db47e591eb1f66ea143230
Source dataset
uspto-grants-2015_05
Patent number
US09023871B2

Reaction notes

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