Hydrochloric Acid → 1,1-Diphenyl-3-(2-piperidyl)propan-2-one

HRID 1579507

反応式

HRID 1579507 の反応式
C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[C:12]1([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH3:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=1.Cl>CO>[C:22]1([CH:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:19](=[O:20])[CH2:21][CH:33]2[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 681612,3,4,5-TetrahydropyridineHCID 699071,1-DiphenylacetoneHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

生成物 1

HCID 123004931,1-Diphenyl-3-(2-piperidyl)propan-2-one収率 37%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

Magnesium methyl carbonate (1.2 moles, 2 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 1,1-diphenylacetone, 63.0 g (0.3 moles), is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen to form the chelate, allowing the methyl alcohol that forms to escape. The mixture is cooled to room temperature under an atmosphere of carbon dioxide and 30.0 g (0.36 moles) of 2,3,4,5-tetrahydropyridine (as α-tripiperidein) is added and stirring continued at room temperature for a period of 6 days under an atmosphere of carbon dioxide. The reaction mixture is poured into 375 ml of concentrated HCl on 400 g of ice and the resulting mixture is extracted with methylene dichloride. The extracts are combined, dried over anhydrous sodium sulfate and the solvent is removed. The crude oil is recrystallized twice from an aqueous isopropyl alcohol solution to yield 37.9 g (37% yield) of 1,1-diphenyl-3-(2-piperidyl)propan- 2-one as the hydrochloride salt having a M.P. of 197-9°C. (dec.)

後処理

  1. customto form the chelate
  2. temperatureThe mixture is cooled to room temperature under an atmosphere of carbon dioxide
  3. stirringstirring
  4. waitcontinued at room temperature for a period of 6 days under an atmosphere of carbon dioxide
  5. extractionthe resulting mixture is extracted with methylene dichloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent is removed
  8. customThe crude oil is recrystallized twice from an aqueous isopropyl alcohol solution

出典と根拠

ORDレコード
ord-ff18898fa2d4456a88ab4fe2beb09e37
出典データセット
uspto-grants-1976_01
特許番号
US03931155

関連ノート

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