Piperidine → HCID 118108311, compound

HRID 2174506Notes

Reaction equation

HRID 2174506 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[C:7]2[CH:14]=O)[CH3:2].[C:16]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)(=[O:18])[CH3:17].N1CCCCC1>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[C:7]2/[CH:14]=[CH:17]/[C:16]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 142824-AcetylpyridineHCID 20400411HCID 20400411, compound

Product 1

HCID 118108311HCID 118108311, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Ethoxy-2-methylindole-3-carboxaldehyde 409a (188 mg, 0.93 mmol) was dissolved in anhydrous methanol (12 mL). 4-Acetylpyridine (168 mg, 1.38 mmol) and piperidine (118 mg, 1.38 mmol) were added and the solution was heated at reflux for 24 h. A precipitate slowly formed which was collected, washed with ice-cold MeOH (30 mL) and dried at 40° C. in a vacuum desiccator for 24 h to yield a bright yellow powder (244 mg, 86%): mp 255-257° C. TLC Rf 0.30 (80% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.88 (s, 1H), 8.80 (m, 2H), 8.09-8.06 (d, 1H, J=15.3 Hz), 7.93-7.92 (m, 2H), 7.41 (d, 1H, J=2.22 Hz), 7.34-7.32 (d, 1H, J=15.3 Hz), 7.30-7.29 (d, 1H, J=8.64 Hz), 6.84-6.82 (dd, 1H, J1=8.7 Hz, J2=2.28 Hz), 4.14-4.11 (q, 2H, J=6.96 Hz), 2.57 (s, 3H), 1.37-1.36 (t, 3H, J=6.96 Hz). 13C NMR (150 MHz, d6-DMSO) δ 188.1, 154.4, 150.6, 145.8, 145.1, 139.6, 131.0, 126.6, 121.4, 112.82, 112.24, 111.3, 109.3, 104.4, 63.6, 14.9, 12.2. Elemental analysis calculated for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14. Found: C, 74.30; H, 6.02; N, 9.04.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 24 h
  3. customA precipitate slowly formed which
  4. customwas collected
  5. washwashed with ice-cold MeOH (30 mL)
  6. customdried at 40° C. in a vacuum desiccator for 24 h

Sources & evidence

ORD record
ord-c6913216f892485992b7b361efc9d690
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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