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

HRID 580386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580386
[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

Komponenten

5

Edukt 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 20135074HCID 20135074, VerbindungHCID 86738843HCID 86738843, Verbindung

Produkt 1

HCID 131715616HCID 131715616, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9079ac7630f348ce848a29413a2a1125
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04752645

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