Hydrochloric Acid → trans-6-(2-Chlorophenyl)cyclohex-3-en-1-amine

HRID 1172320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172320
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-])=O)[CH2:12][CH:11]=[CH:10][CH2:9]1.Cl.C([O-])(O)=O.[Na+]>CO.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([NH2:14])[CH2:12][CH:11]=[CH:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68771799HCID 68771799, Verbindung

Produkt 1

HCID 68772117trans-6-(2-Chlorophenyl)cyclohex-3-en-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of Example 1A (100 mg, 0.042 mmol) in a 2 mL solution of 1:1 aqueous concentrated HCl in methanol at 0° C., Zn dust (32 mg, 0.5 mmol) was added in several portions. The solution was allowed to warm to room temperature over three hours. Afterwards, the solution was carefully basified with saturated NaHCO3. The mixture was extracted with ethyl acetate, concentrated, taken up in dichloromethane, and filtered through Celite. Concentration of the filtrate gave the title compound. 1H NMR (300 MHz, C5D5N) δ ppm 7.41-7.43 (m, 2H), 7.24-7.28 (m, 1H), 7.12-7.14 (m, 1H), 5.70-5.73 (m, 2H), 3.49-3.54 (m, 2H), 2.55-2.58 (m, 1H), 2.37-2.41 (m, 1H), 2.14-2.24 (m, 2H). MS (ESI+) m/z 208 (M+H)+

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. concentrationconcentrated
  3. filtrationfiltered through Celite

Quellen und Nachweise

ORD-Eintrag
ord-ab50b131a7394623a7e4964f9d1534f1
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834012B2

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