1,2-Dichloroethane → N'-benzo[1,2,5]thiadiazol-4-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine

HRID 1179061

Reaktionsgleichung

Reaktionsgleichung von HRID 1179061
[N:1]1[S:5][N:4]=[C:3]2[C:6]([NH2:10])=[CH:7][CH:8]=[CH:9][C:2]=12.[CH3:11][N:12]([CH3:26])[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:45]CCCl>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([NH:10][CH:16]3[CH2:15][CH2:14][C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]3)=[CH:7][CH:8]=[CH:9][C:2]=12.[ClH:45].[ClH:45].[N:1]1[S:5][N:4]=[C:3]2[C:6]([NH:10][CH:16]3[CH2:15][CH2:14][C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]3)=[CH:7][CH:8]=[CH:9][C:2]=12

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 698452,1,3-Benzothiadiazol-4-amineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Produkt 2

HCID 10291627N'-benzo[1,2,5]thiadiazol-4-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamineHCID 69338031N'-Benzo[1,2,5]thiadiazol-4-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride

Versuchsvorschrift

302 mg Benzo[1,2,5]thiadiazol-4-ylamine and 435 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry 1,2-dichloroethane (20 ml) under argon. Glacial acetic acid (2 mmol) and 600 mg sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for 24 hours at RT. For working up, the reaction mixture was concentrated and the residue was adjusted to pH 11 with five molar sodium hydroxide solution. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (3×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 40 mg of the polar diastereomer of N′-benzo[1,2,5]thiadiazol-4-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a red solid, from which the corresponding hydrochloride was precipitated with 1.85 M ethanolic hydrochloric acid (0.15 ml) in 2-butanone (2 ml) (35 mg; m.p. 122-125° C.).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. additionThe alkaline phase was diluted with water (10 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0883b7d055ce4942a04088d47f429c0e
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276518B2

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