Reaction equation
[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.[C:15]12([NH2:25])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.[C:26](O)(=O)[CH3:27]>>[C:15]12([N:25]3[CH2:5][CH2:6][C:11]4[C:10]5[CH:9]=[CH:8][CH:7]=[CH:27][C:26]=5[CH2:4][CH2:3][C:2]=4[CH2:1]3)[CH2:22][CH:21]3[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]3)[CH2:16]1)[CH2:24]2Participants
Procedure
Following the procedure of Example 1, step 3, 2.05 g (14.0 mmol) of 1-methyl-3,4-dihydronaphthalene in 14 ml of acetic acid was reacted with 4.54 ml of 37% formaldehyde solution and 6.03 g of 1-adamantanamine hydrochloride. Work up gave 5.58 g of crude 3-(1-adamantyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline. Following the procedure of Example 2, this was reacted with 1.02 g of lithium wire in 400 ml of liquid ammonia, 100 ml of anhydrous THF and 2 ml of aniline. Chromatography on flash silica, eluting with 5-20% methanol/dichloromethane, then on alumina, eluting with 2-7% ethyl acetate/petroleum ether, afforded 0.54 g (12%) 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 methanol/petroleum ether, the title product hydrochloride was obtained as a white solid, m.p. 252°-255° C. NMR δ(D2O, CD3CN) 1.56 (1H, m), 1.68-1.92 (9H, m), 2.02-2.04 (6H, m), 2.27 (3H, s), 2.61 (1H, m), 2.74 (1H, d of d), 2.82 (1H, t, J=12.0 Hz), 2.92-2.95 (2H, m), 3.08 (1H, t of d), 3.65 (1H, m), 3.82 (1H, m), 7.19-7.23 (3H, m), 7.29-7.30 (1H, m). m/z (CI+, NH3) 322 (M+H)+, 195. Analysis calcd. for C23H32ClN: C, 77.17; H, 9.01; N, 3.91%. Found: C, 77.09; H, 8.95; N, 3.89%.
Sources & evidence
- ORD record
- ord-65ee8338eb794e8fb518cde266d690ef
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294618
Linked notes
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