Reaktionsgleichung
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]=1.C=O.Cl.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:22](O)(=O)[CH3:23]>>[CH:15]1([N:21]2[CH2:5][CH2:6][C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[CH:23][C:22]=4[CH2:4][CH2:3][C:2]=3[CH2:1]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1Komponenten
Versuchsvorschrift
Following the procedure of Example 1, step 3, 1.00 g (6.93 mmol) of 1-methyl-3,4-dihydronaphthalene in 7 ml of acetic acid was reacted with 2.25 ml of 37% formaldehyde solution and 2.16 g of cyclohexylamine hydrochloride. Work up gave 2.41 g of crude 3-cyclohexyl-1,2,3,4,5,6-hexahydro-benz[f]isoquinoline. Following the procedure of Example 2, this was reacted with 0.397 g of lithium wire in 200 ml of liquid ammonia, 40 ml of anhydrous THF and 1 ml of aniline. Chromatography on silica, eluting with 5-10% methanol/dichloromethane, then on alumina, eluting with 5-7% ethyl acetate/petroleum ether gave 0.333 g (18%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent, the title product hydrochloride was obtained as a white solid, m.p. 281°-285° C. (dec). NMR δ(D2O) 1.16-1.96 (12H, m), 2.10 (2H, m), 2.69 (2H, m), 2.92-3.05 (3H, m), 3.20-3.31 (2H, m), 3.55 (1H, m), 3.69 (1H, m), 7.25-7.29 (3H, m), 7.35-7.36 (1H, m). m/z (CI+, NH3) 270 (M+H)+, 226.
Quellen und Nachweise
- ORD-Eintrag
- ord-f4d1fd9197a944438d871783f9202db4
- Quelldatensatz
- uspto-grants-1994_03
- Patentnummer
- US05294618
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