1,2-Dichloroethane → N'-cyclooctyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine

HRID 1179065

Reaktionsgleichung

Reaktionsgleichung von HRID 1179065
[CH:1]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][N:11]([CH3:25])[C:12]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C>[CH:1]1([NH:9][CH:15]2[CH2:14][CH2:13][C:12]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([N:11]([CH3:25])[CH3:10])[CH2:17][CH2:16]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 2903CyclooctylamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Produkt 1

HCID 9901994N'-cyclooctyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamineAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

254 mg Cyclooctylamine and 434 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry tetrahydrofuran (15 ml) and 1,2-dichloroethane (5 ml) under argon. Glacial acetic acid (120 mg) and 600 mg sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for 18 hours at RT. For working up, the reaction mixture was concentrated and the residue was washed with one molar hydrochloric acid (20 ml) and with ether (2×30 ml). The aqueous phase was rendered alkaline with five molar sodium hydroxide solution and extracted with ether (3×30 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product (515 mg) was chromatographed over silica gel with methanol. 108 mg N′-cyclooctyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a colorless oil, from which the corresponding dihydrochloride was precipitated with 3.3 M ethanolic hydrochloric acid (0.25 ml) in 2-butanone (2 ml) (102 mg; m.p. 247-249° C.).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. washthe residue was washed with one molar hydrochloric acid (20 ml) and with ether (2×30 ml)
  3. extractionextracted with ether (3×30 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product (515 mg) was chromatographed over silica gel with methanol

Quellen und Nachweise

ORD-Eintrag
ord-7a75a0f41e9b4ca5871492a26b9d6449
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276518B2

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