Potassium Carbonate → HCID 22850900, compound
Reaction equation
[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CN(C=O)C>[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:3]2[CH2:2][CH2:1][C@@H:10]3[C@H:5]([CH2:6][CH2:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)[CH2:4]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the procedure of Example 3, step 4, 0.153 g (0.815 mmol) of crude trans-1,2,3,4,4a, 5,6,10b-octahydrobenz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.124 g (0.897 mmol) of anhydrous potassium carbonate and 0.184 g (0.852 mmol) of 4-nitrobenzyl bromide. Chromatography on flash silica, eluting with 30-40% ethyl acetate/petroleum ether, gave 0.052 g (20%) 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/methanol, the title product hydrochloride was obtained as a white solid, m.p. 198°-201° C. NMR δ(D2O/CD3CN) 1.45-1.57 (1H, m), 1.61-1.74 (1H, m), 1.79-1.83 (2H, m), 2.60-2.69 (2H, m), 2.88-2.94 (3H, m), 3.20 (1H, t, of d), 3.44 (1H, m), 3.64 (1H, m), 4.44 (2H, d, J=2.9 Hz), 7.17-7.22 (3H, m), 7.26-7.28 (1H, m), 7.77 (2H, d, J=8.8 Hz), 8.34 (2H, d, J=8.8 Hz). m/z (CI+, NH3) 323 (M+H)+, 308 (M-O+H)+, 248, 211, 174, 133, 106. Analysis calcd. for C22H28ClN: C, 66.94; H, 6.46; N, 7.81%. Found: C, 66.83; H, 6.49; N, 7.81%.
Workup
- washChromatography on flash silica, eluting with 30-40% ethyl acetate/petroleum ether
Sources & evidence
- ORD record
- ord-44f84f08d87f435db4d7adc7fc35d0a1
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294618
Reaction notes
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