2-(Dimethylamino)ethanol → (6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanone

HRID 404224

반응식

HRID 404224 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(C)CCO.CON(C)[C:22]([CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:23]>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])[N:3]=1

참가 물질

6

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 79772-ChloropyridineHCID 23499459N-Methoxy-N,1-dimethylpiperidine-4-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 10705139(6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanone수율 47.6%

시약·촉매·용매 1

HCID 8058Hexane용매2회

실험 절차

Add 2-chloropyridine (1 g, 8.8 mmole) to a mixture of n-butyl lithium (1.6 M in hexane) (22 mL, 35.2 mmole) and 2-dimethylamino-ethanol (1.56 g, 17.6 mmole) in hexane (20 mL at −78° C.) and stirred for 1 hour. Then add 1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide (3.2 g, 17.6 mmole) in hexane (5 mL) and stir the mixture for 1 hour. Quench the reaction mixture with water and extract twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, evaporate the solvent and purify the residual product by chromatography on a silica gel column to give about 1 g of the title product.

후처리

  1. customQuench the reaction mixture with water
  2. extractionextract twice with ethyl acetate
  3. dry with materialdry the organic layer with anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify the residual product by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-aba5696c17414b9991c86a87aeb18a46
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748459B2

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