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]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH:16]1[NH2:25])[CH2:22]2.[C:26](O)(=O)[CH3:27]>>[CH:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH:16]1[N:25]1[CH2:5][CH2:6][CH:11]3[CH:2]([CH2:3][CH2:4][C:26]4[CH:27]=[CH:7][CH:8]=[CH:9][C:10]=43)[CH2:1]1)[CH2:22]2Komponenten
Versuchsvorschrift
Following the procedure of Example 1, step 3, 5.00 g (34.7 mmol) of 1-methyl-3,4-dihydronaphthalene in 35 ml of acetic acid was reacted with 11.3 ml of 37% formaldehyde solution and 14.96 g of 2-adamantanamine hydrochloride. Work up gave 14.47 g of crude 3-(2-adamantyl)-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline. Following the procedure of Example 2, this was reacted with 2.09 g of lithium wire in 500 ml of liquid ammonia, 200 ml of anhydrous THF and 5 ml of aniline. Chromatography on flash silica, eluting with 2-10% methanol/dichloromethane, then on alumina, eluting with 0-4% ethyl acetate/petroleum ether, gave 2.73 g (24%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent and recrystallisation from ethanol/ethyl acetate/petroleum ether, the title product hydrochloride was obtained as a white solid, m.p. 247°-252° C. NMR δ(D2O/CD3CN) 1.52 (1H, m), 1.69-1.98 (15H, m), 2.48 (2H, s), 2.59-2.75 (3H, m), 2.91-3.09 (3H, m), 3.29-3.34 (1H, m), 3.79 (1H, m), 3.95 (1H, m), 7.18-7.24 (3H, m), 7.30-7.33 (1H, m). m/z (CI+, NH3) 322 (M+H)+.
Quellen und Nachweise
- ORD-Eintrag
- ord-a20fc5f9e6e947f6862bcee3b54766a8
- Quelldatensatz
- uspto-grants-1994_03
- Patentnummer
- US05294618
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