Water → HCID 54245555, compound

HRID 861033Notes

Reaction equation

HRID 861033 reaction equation
[C:1]1([CH3:9])[C:2]([CH:7]=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[OH2:16].[C:17]1([CH3:23])C=CC=C[CH:18]=1>>[CH3:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[C:18]([C:13]1[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=1)[C:17](=[O:16])[CH3:23]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8082PiperidineHCID 107222-Methylbenzaldehyde

Product 1

HCID 54245555HCID 54245555, compound

Procedure

A solution of 4-pyrridylacetone (Example A-5, step 1) (0.75 g, 5.56 mmol), o-tolualdehyde (0.73 g, 5.56 mmol) and piperidine (100 mg) in toluene (50 ml) was heated to reflux. Water generated during the reaction was removed by a Dean-Stark trap. After heating at reflux for 5 hours, the reaction mixture was stirred at room temperature for 15 hours. The mixture was concentrated to an orange color oily residue. The crude ketone was purified by chromatography to give 4-(2-methylphenyl)-3-(4-pyridyl)-3-butene-2-one: Anal. Calc'd for C16H15NO (237.30): C, 80.98; H, 6.37; N, 5.90. Found: C, 80.78; H, 6.61; N, 5.85.

Workup

  1. customwas removed by a Dean-Stark trap
  2. temperatureAfter heating
  3. temperatureat reflux for 5 hours
  4. concentrationThe mixture was concentrated to an orange color oily residue
  5. customThe crude ketone was purified by chromatography

Sources & evidence

ORD record
ord-e1ecc96c967c4c3f87d7f588c7b79880
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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