Pyridine → 4-Chloro-N-(1-phenyl-cyclohexyl)-butyramide

HRID 2235200노트

반응식

HRID 2235200 반응식
[C:1]1([C:7]2([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[Cl:20][CH2:21][CH2:22][CH2:23][C:24]([NH:13][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:25]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 318621-PhenylcyclohexylamineHCID 783704-Chlorobutyryl chloride

생성물 1

HCID 592994904-Chloro-N-(1-phenyl-cyclohexyl)-butyramide수율 89.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Dissolve 1-phenyl-cyclohexylamine (Preparation 28) (0.41 g, 2.32 mmol) in dichloromethane (50 mL) and cool to 0° C. Add pyridine (1.18 g, 11.61 mmol) and 4-chloro-butyryl chloride (0.65 g, 4.64 mmol). Stir the reaction mixture for one hour under nitrogen. Add water (50 mL), and extract the aqueous layer with ethyl acetate (3×100 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 10-50% of EtOAc/Hexane) to give 0.58 g (89%) of the title compound as a colorless oil.

후처리

  1. extractionAdd water (50 mL), and extract the aqueous layer with ethyl acetate (3×100 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 10-50% of EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-1834edc6add5476d8918ccf55c4c67b0
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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