Potassium Iodide → N-[3-[4-(methylthio)phenoxy]propyl]octylamine

HRID 26005

반응식

HRID 26005 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1.[CH2:14]([NH2:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[I-].[K+]>C(O)C>[CH3:13][S:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:22][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 4875Potassium IodideHCID 8143OctylamineHCID 12928626Benzene, 1-(3-chloropropoxy)-4-(methylthio)-

생성물 1

HCID 21326176N-[3-[4-(methylthio)phenoxy]propyl]octylamine수율 22%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 1-chloro-3-[4-(methylthio)phenoxy]propane (5.0 g., 0.023 mole) in 30 ml. of ethanol is treated with n-octylamine (2.84 g., 0.022 mole) and 30 mg. of potassium iodide. After refluxing for a period of 18 hrs., the reaction mixture is concentrated to dryness under reduced pressure, treated with 3N potassium hydroxide solution and ether, and the layers separated. The ether layer is washed with water, concentrated under reduced pressure, and heated on a steam bath at 0.1 mm Hg pressure to remove residual n-octylamine. The residue of N-[3-[4-(methylthio)phenoxy]propyl]octylamine base thus obtained is dissolved in ethanol, treated with excess 6N hydrochloric acid and activated charcoal, filtered and concentrated to dryness under reduced pressure. Crystallization of the residue from isopropyl alcohol-ether affords 1.7 g. (22% yield) of analytically pure N-[3-[4-(methylthio)phenoxy]propyl]octylamine hydrochloride, m.p. 214.5°-215.5° C. (corr.).

후처리

  1. temperatureAfter refluxing for a period of 18 hrs
  2. concentration, the reaction mixture is concentrated to dryness under reduced pressure
  3. additiontreated with 3N potassium hydroxide solution and ether
  4. customthe layers separated
  5. washThe ether layer is washed with water
  6. concentrationconcentrated under reduced pressure
  7. temperatureheated on a steam bath at 0.1 mm Hg pressure
  8. customto remove residual n-octylamine

출처 및 근거

ORD 기록
ord-97493774cbfa4cd8a6eab4fe091d5a9d
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147805

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