2-Chloro-N,N-dimethylethylamine → HCID 131715616, 화합물

HRID 580386노트

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HRID 580386 반응식
[H-].[Na+].CCCCCC.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH:17]([CH2:21][CH3:22])[CH:16]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:15][C:14]=2[CH:31]=1.[CH3:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34]>CN(C)C=O>[ClH:9].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]([CH2:36][CH2:35][N:33]([CH3:34])[CH3:32])[C:18](=[O:20])[C@@H:17]([CH2:21][CH3:22])[C@@H:16]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH2:15][C:14]=2[CH:31]=1

참가 물질

5

반응물 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 20135074HCID 20135074, 화합물HCID 86738843HCID 86738843, 화합물

생성물 1

HCID 131715616HCID 131715616, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

To a slurry of prewashed (hexane) sodium hydride (~50% in mineral oil) (0.064 g; 1.34 mmole; 1.2 eq.) in dry dimethylformamide (10 ml) was added 7-chloro-3-ethyl-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (370 mg; 1.12 mmole). After stirring the mixture at 25° C. for 1 hour, 3.2 ml (5.6 mmole) of 1.7N N,N-dimethyl-2-chloroethylamine (in toluene) was added, and the solution was heated at 80° C. for 24 hours. The reaction was quenched with 1N hydrochloric acid, made basic with 50% sodium hydroxide solution, extracted with ethyl acetate (two times) and dried (magnesium sulfate). After solvent removal, 0.49 g of a brown oil remained. This crude product was flash chromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 2:1-hexane: ethyl acetate, followed by 1:1-hexane: ethyl acetate, followed by ethyl acetate). Those fractions which contained the cis amine product were dissolved into ether. The salt was precipitated out by the dropwise addition of hydrogen chloride saturated ether solution. The resultant white solid was collected by suction-filtration, yielding 200 mg. The lower Rf trans isomer of the title compound was likewise obtained (10 mg) as well as a cis-trans mixture (50 mg), and unreacted starting material (40 mg).

후처리

  1. temperaturethe solution was heated at 80° C. for 24 hours
  2. customThe reaction was quenched with 1N hydrochloric acid
  3. extractionextracted with ethyl acetate (two times)
  4. dry with materialdried (magnesium sulfate)
  5. customAfter solvent removal, 0.49 g of a brown oil
  6. customchromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 2:1-hexane: ethyl acetate, followed by 1:1-hexane: ethyl acetate, followed by ethyl acetate)
  7. dissolutionwere dissolved into ether
  8. customThe salt was precipitated out by the dropwise addition of hydrogen chloride saturated ether solution
  9. filtrationThe resultant white solid was collected by suction-filtration
  10. customyielding 200 mg

출처 및 근거

ORD 기록
ord-9079ac7630f348ce848a29413a2a1125
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752645

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