Hydrochloric Acid → 4-(3-Methoxypropoxy)piperidine

HRID 354841노트

반응식

HRID 354841 반응식
C([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=O)C.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][O:17][CH3:18].[Cl-].[Na+].Cl>CN(C)C=O>[CH3:18][O:17][CH2:16][CH2:15][CH2:14][O:10][CH:7]1[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropaneHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

생성물 1

HCID 205064044-(3-Methoxypropoxy)piperidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A solution of N-acetyl-4-hydroxypiperidine (30.5 g.) in dimethylformamide (200 ml.) is added dropwise to a stirred suspension of sodium hydride (11.26 g., 50% dispersion in mineral oil) in dimethylformamide (300 ml.) under an atmosphere of nitrogen. The reaction temperature is kept below 30° C. by external cooling and, after the addition is complete, stirring is continued for a further 11/4 hours. A solution of 1-bromo-3-methoxypropane (35.2 g.) in dimethylformamide (100 ml.) is then added dropwise with external cooling, and the resulting clear solution is stirred at room temperature overnight. The reaction mixture is then evaporated in vacuo, the residue partitioned between water and chloroform, the organic extracts dried (Na2SO4) and evaporated to leave a crude residue. The above aqueous phase is saturated with sodium chloride, further extracted with chloroform, and the organic phase is dried (Na2SO4), and evaporated to leave a further residue. This residue is combined with the original residue and heated on a steam bath overnight with hydrochloric acid (243 ml., 2N). The reaction mixture is extracted with chloroform to remove the residual mineral oil, the aqueous phase concentrated, basified with sodium hydroxide (pH 12), then reextracted with chloroform. The organic extracts are washed with brine, dried (Na2SO4) and evaporated to afford the desired product.

후처리

  1. customis kept below 30° C.
  2. temperatureby external cooling
  3. additionafter the addition
  4. custom4 hours
  5. stirringthe resulting clear solution is stirred at room temperature overnight
  6. customThe reaction mixture is then evaporated in vacuo
  7. customthe residue partitioned between water and chloroform
  8. dry with materialthe organic extracts dried (Na2SO4)
  9. customevaporated
  10. customto leave a crude residue
  11. extractionfurther extracted with chloroform
  12. dry with materialthe organic phase is dried (Na2SO4)
  13. customevaporated
  14. customto leave a further residue
  15. extractionThe reaction mixture is extracted with chloroform
  16. customto remove the residual mineral oil
  17. concentrationthe aqueous phase concentrated
  18. washThe organic extracts are washed with brine
  19. dry with materialdried (Na2SO4)
  20. customevaporated

출처 및 근거

ORD 기록
ord-bd5972c36990441fb127200f2114d9f4
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377581

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