Carbon Dioxide → HCID 21567714、化合物

HRID 1579502

反応式

HRID 1579502 の反応式
C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[C:22](=[O:24])[CH3:23].C(=O)=O.[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=1.C1CC2N(C3N(C4N2CCCC4)CCCC3)CC1>CN(C)C=O.C(OCC)C.CO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[C:22](=[O:24])[CH2:23][CH:33]1[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]1

参加物

9

反応物 5

HCID 280Carbon Dioxide2 回HCID 681612,3,4,5-TetrahydropyridineHCID 709912',5'-DimethoxyacetophenoneHCID 136344Dodecahydro-4H,8H,12H-4a,8a,12a-triazatriphenyleneHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

生成物 1

HCID 21567714HCID 21567714、化合物収率 85.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Magnesium methyl carbonate (approximately 1 mole of a 2 M solution in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide and 45.0 g (0.25 mole) of 2',5'-dimethoxyacetophenone added thereto. Nitrogen is substituted for the carbon dioxide and the mixture is stirred at 120°C. for 5 hours while allowing the methanol that forms to escape. The mixture is cooled under carbon dioxide and 25.3 g (0.30 mole) of 2,3,4,5-tetrahydropyridine (as the trimer, α-tripiperidein) added. The resulting mixture is stirred at room temperature in an atmosphere of carbon dioxide for 40 hours, poured into 3 liters of ethyl ether and the resulting precipitate is collected by filtration. The filtrate is acidified with a mixture of 300 ml of concentrated HCl-ice and the resulting precipitate is collected by filtration. The filtrate is made alkaline with 2N NaOH, extracted with ethyl ether, the extracts dried (Na2SO4) and the solvent removed. The resulting oily residue is converted to the hydrochloride salt by the addition of isopropanolic HCl. The two portions are combined and recrystallized from isopropanolwater to yield 56.0 g (75% of theory) of 2',5'-dimethoxy-2-(2-piperidyl)acetophenone as the hydrochloride salt having a M.P. of 186°-188°C. (dec.)

後処理

  1. temperatureThe mixture is cooled under carbon dioxide
  2. filtrationthe resulting precipitate is collected by filtration
  3. additionThe filtrate is acidified with a mixture of 300 ml of concentrated HCl-ice
  4. filtrationthe resulting precipitate is collected by filtration
  5. extractionextracted with ethyl ether
  6. dry with materialthe extracts dried (Na2SO4)
  7. customthe solvent removed
  8. additionThe resulting oily residue is converted to the hydrochloride salt by the addition of isopropanolic HCl
  9. customrecrystallized from isopropanolwater

出典と根拠

ORDレコード
ord-93118804755d4389ade386183f9549f0
出典データセット
uspto-grants-1976_01
特許番号
US03931155

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