2-Chloro-N,N-dimethylethylamine → 2,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)chroman

HRID 614738

반응식

HRID 614738 반응식
[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:22])=[CH:7][CH:8]=2)[O:3]1.[H-].[Na+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:22][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[CH:7][CH:8]=2)[O:3]1

참가 물질

6

반응물 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 205705012,2-Dimethyl-4-(1-naphthyl)-7-chromanol

생성물 1

HCID 205705522,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)chroman수율 67.2%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

To a stirred solution of 2,2-dimethyl-4-(1-naphthyl)-7-chromanol (7.48 g) in dry toluene (50 ml) was added sodium hydride (1.5 g, ~1.5 eq., 60% dispersion in oil) and the mixture was brought to reflux. To the resulting solution was added dropwise over 10 minutes a solution of 2-dimethylaminoethyl chloride (2.70 g, ~1.1 eq.) in dry toluene (10 ml) and the mixture was stirred under reflux for 2 hours, cooled, diluted with water and left to stand overnight. Next day the toluene layer was separated and evaporated in vacuo. The aqueous layer was extracted with ether and the extract used to dissolve the residue from the toluene evaporation. The organic layer was extracted with 5N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid extract was basified and extracted into ether. After being dried the ether was removed in vacuo to give a yellow oil (6.2 g) which was chromatographed on alumina in 8% ether -- 92% petroleum ether (b.p. 60-80) to give the title compound (4.71 g, 51%) as a colourless oil. The hydrochloric salt had m.p. 178.5°-181.5° C.

후처리

  1. temperatureto reflux
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. waitleft
  5. customNext day the toluene layer was separated
  6. customevaporated in vacuo
  7. extractionThe aqueous layer was extracted with ether
  8. dissolutionto dissolve the residue
  9. customfrom the toluene evaporation
  10. extractionThe organic layer was extracted with 5N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid
  11. extractionextract
  12. extractionextracted into ether
  13. dry with materialAfter being dried the ether
  14. customwas removed in vacuo

출처 및 근거

ORD 기록
ord-385a11afc3704a58be3f3869dea04a6d
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04146539

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