Carbon Dioxide → HCID 12300451, compound

HRID 1579503Notes

Reaction equation

HRID 1579503 reaction equation
C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[CH2:12]([C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=1.C1CC2N(C3N(C4N2CCCC4)CCCC3)CC1.C(=O)=O.Cl>CO>[CH2:12]([C:24]1[CH:25]=[CH:26][C:27]([C:30](=[O:32])[CH2:31][CH:38]2[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]2)=[CH:28][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 681612,3,4,5-TetrahydropyridineHCID 80582p-LaurylacetophenoneHCID 136344Dodecahydro-4H,8H,12H-4a,8a,12a-triazatriphenyleneHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

Product 1

HCID 12300451HCID 12300451, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Magnesium methyl carbonate (0.5 mole 1 M in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 4'-dodecylacetophenone, 28.9 g (0.1 mole), is added, and the mixture stirred at 120°C. for 4 hours under a stream of nitrogen, allowing the methanol that forms to escape. The reaction mixture is cooled to room temperature under an atmosphere of carbon dioxide and 10.1 g (0.12 mole) of 2,3,4,5-tetrahydropyridine trimer (α-tripiperidein) is added. The mixture is stirred at room temperature for 66 hours in an atmosphere of carbon dioxide and poured into a solution 800 ml of 2N HCl. The solid is removed by filtration, dissolved in methylene dichloride, dried over anhydrous sodium sulfate and azeotroped with methyl ether until the product precipitates. The 4'-dodecyl-2-(2-piperidyl)acetophenone, when recrystallized as the hydrochloride salt from a methylene dichloride-ethyl ether mixture, is obtained in 80% yield, (32.5 g) and has a M.P. of 126-7°C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature under an atmosphere of carbon dioxide
  2. customThe solid is removed by filtration
  3. dissolutiondissolved in methylene dichloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customazeotroped with methyl ether until the product
  6. customprecipitates
  7. customThe 4'-dodecyl-2-(2-piperidyl)acetophenone, when recrystallized as the hydrochloride salt from a methylene dichloride-ethyl ether mixture
  8. customis obtained in 80% yield, (32.5 g)

Sources & evidence

ORD record
ord-18c06bb23a9f487691b80b6681a599c4
Source dataset
uspto-grants-1976_01
Patent number
US03931155

Reaction notes

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