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.[CH3:15][NH2:16].[C:17](O)(=O)[CH3:18]>>[CH3:15][N:16]1[CH2:5][CH2:6][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:18][C:17]=3[CH2:4][CH2:3][C:2]=2[CH2:1]1Komponenten
5
Versuchsvorschrift
Following the procedure of Example 1, step 3, 10 g (70 mmol) of 1-methyl-3,4-dihydronaphthalene and 22.55 g (278 mmol) of 37% formaldehyde solution in 60 ml of acetic acid were reacted with 10.8 g (0.16 mol) of methylamine hydrochloride. Chromatography on flash silica, eluting with 10% methanol/dichloromethane gave 6.0 g (44%) of the title product as a yellow oil. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent and recrystallisation from ethyl acetate/ethanol, the title product hydrochloride was obtained, m.p. 198°-200° C. NMR δ(D2O) 2.23 (2H, t), 2.74-3.01 (7H, m), 3.35 (1H, m), 3.72 (1H, m), 3.90-3.95 (2H, m), 7.27-7.33 (4H, m). m/z (FAB+) 200 (M+H)+.
Aufarbeitung
- washChromatography on flash silica, eluting with 10% methanol/dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-fd790897546842699c7e7d646766dadb
- Quelldatensatz
- uspto-grants-1994_03
- Patentnummer
- US05294618
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