2-Chloro-N,N-dimethylethylamine → HCID 131715616、化合物

HRID 580386ノート

反応式

HRID 580386 の反応式
[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

参加物

5

反応物 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 20135074HCID 20135074、化合物HCID 86738843HCID 86738843、化合物

生成物 1

HCID 131715616HCID 131715616、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9079ac7630f348ce848a29413a2a1125
出典データセット
uspto-grants-1988_06
特許番号
US04752645

反応ノート

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