2,3,4,5-Tetrahydropyridine → HCID 53954090, compound

HRID 1579505Notes

Reaction equation

HRID 1579505 reaction equation
C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[CH3:12][C:13](=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:14]=[CH:15][C:16](=[O:18])[CH3:17].[N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=1>CO>[CH3:12][C:13](=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:14]=[CH:15][C:16](=[O:18])[CH2:17][CH:31]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1

Participants

5

Reactant 3

HCID 681612,3,4,5-TetrahydropyridineHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)HCID 543565705-Methyl-6-phenyl-3,5-hexadien-2-one

Product 1

HCID 53954090HCID 53954090, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Magnesium methyl carbonate (1.2 moles, 2 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 5-methyl-6-phenyl-3,5-hexadien-2-one, 53.0 g (0.285 mole) is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen while permitting the methanol that forms to escape. The mixture is allowed to cool under an atmosphere of carbon dioxide and 57.0 g (0.68 mole) of 2,3,4,5-tetrahydropyridine (as α-tripiperidein) is added and stirred at room temperature under an atmosphere of carbon dioxide for a period of 70 hours. The reaction mixture is poured into a concentrated HCl-ice mixture and extracted with methylene dichloride. The extracts are combined, washed with water, dried over anhydrous sodium sulfate, and the solvent removed. The crude 5-methyl-6-phenyl-1-(2-piperidyl)-3,5-hexadein-2-one which remains is recrystallized twice from isopropyl alcohol as the hydrochloride salt and is obtained in 48% yield (41.6 g) and has a M.P. of 179-80°C.

Workup

  1. temperatureto cool under an atmosphere of carbon dioxide
  2. stirringstirred at room temperature under an atmosphere of carbon dioxide for a period of 70 hours
  3. extractionextracted with methylene dichloride
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent removed
  7. customThe crude 5-methyl-6-phenyl-1-(2-piperidyl)-3,5-hexadein-2-one which remains is recrystallized twice from isopropyl alcohol as the hydrochloride salt
  8. customis obtained in 48% yield (41.6 g)

Sources & evidence

ORD record
ord-fa6b7a3045384436ae45b1a518257bc9
Source dataset
uspto-grants-1976_01
Patent number
US03931155

Reaction notes

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