6-(Piperidin-1-yl)pyridine-3-carbaldehyde → HCID 46841709, compound

HRID 1846343Notes

Reaction equation

HRID 1846343 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[N:21]1([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][N:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CCO>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:1]=[C:31]2[C:30]2[CH:29]=[N:28][C:27]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:34][CH:33]=2)=[CH:8][CH:9]=1)([CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 27639806-(Piperidin-1-yl)pyridine-3-carbaldehydeHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamide

Product 1

HCID 46841709HCID 46841709, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-N-(4-sec-butylphenyl)benzamide (0.350 g, 1.3 mmol) and 6-(piperidin-1-yl)nicotinaldehyde (1.3 mmol) were mixed in anyhydrous EtOH (40 mL) and anyhydrous CuCl2 (0.524 g, 3.9 mmol) was added. The reaction mixture was heated at reflux for 3 hours, cooled to room temperature, and stirred overnight. The reaction mixture was concentrated, diluted with ethyl acetate (150 mL), washed with water (2×100 mL), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 80% ethyl acetate/heptane, afforded the title compound as a white solid (35%) as a white solid. 1H-NMR (300 MHz, DMSO-d6): δ 8.14-8.17 (m, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.85-7.90 (m, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.53-7.58 (m, 1H), 7.35 (d, J=6.5 Hz, 1H), 7.17-7.24 (m, 4H), 6.55 (d, J=9.1 Hz, 1H), 3.40-3.49 (m, 4H), 2.57-2.66 (m, 1H), 1.44-1.64 (m, 8H), 1.19 (d, J=6.9 Hz, 3H), 0.68 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 439 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with ethyl acetate (150 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 80% ethyl acetate/heptane

Sources & evidence

ORD record
ord-dfa21d26983c4dbcb00c83e258bd2511
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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