Dimethylformamide → 1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester

HRID 1165209노트

반응식

HRID 1165209 반응식
Cl.[CH3:2][O:3][C:4](=[O:11])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Br[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][N:8]2[CH2:9][CH2:10][CH:5]([C:4]([O:3][CH3:2])=[O:11])[CH2:6][CH2:7]2)=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 187838294-Piperidinecarboxylic acid, methyl ester, hydrochloride (1:1)

생성물 1

HCID 108695871-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

To a stirred, room temperature, mixture of isonipecotic acid methyl ester hydrochloride (5.00 g, 2.78×10-2 mole), potassium carbonate (7.70 g, 5.57×10-2 mole), and DMF (100 ml) was added 1-(2-bromoethyl)-4-methoxybenzene (5.99 g, 2.78×10-2 mole). The reaction was then immersed in an oil bath which had been preheated to ca. 90° C. The reaction was heated at ca. 90° C. for ca. 17 hours and was then poured into a separatory funnel containing water and a 2:1 mixture of ethyl acetate:toluene. The two phases were mixed and the aqueous layer was separated. The organic layer was washed two times with H20 and once with saturated aqueous NaCl before being dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving an oil. Purification by flash chromatography (ethyl acetate) and crystallization from cyclohexane gave 1-[2-(4-methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester as a colorless solid: 3.98 g (52%), m.p. 66°-68° C.

후처리

  1. customThe reaction was then immersed in an oil bath
  2. customhad been preheated to ca. 90° C
  3. additionwas then poured into a separatory funnel
  4. additionThe two phases were mixed
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed two times with H20
  7. dry with materialonce with saturated aqueous NaCl before being dried over anhydrous Na2SO4
  8. customThe drying agent was removed by filtration
  9. customthe filtrate was evaporated at reduced pressure
  10. customleaving an oil
  11. customPurification
  12. customby flash chromatography (ethyl acetate) and crystallization from cyclohexane

출처 및 근거

ORD 기록
ord-fb31df28cb904399958f902dedbdbfcd
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04908372

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