Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1) → alpha-(3,4-Dimethoxyphenyl)-1-[(3,4-dimethoxyphenyl) methyl]-3,4-dihydro-6,7-dimethoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[NH:19][CH2:18][CH2:17][C:16]3[C:11]2=[CH:12][C:13]([O:22][CH3:23])=[C:14]([O:20][CH3:21])[CH:15]=3)=[CH:5][C:4]=1[O:24][CH3:25].Cl.I[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([S:46][C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1)([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[C:34]#[N:35]>>[CH3:45][O:44][C:38]1[CH:37]=[C:36]([C:33]([S:46][C:47]2[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=2)([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:19]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][C:13]([O:22][CH3:23])=[C:14]([O:20][CH3:21])[CH:15]=3)[CH:10]2[CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:24][CH3:25])[CH:5]=2)[C:34]#[N:35])[CH:41]=[CH:40][C:39]=1[O:42][CH3:43]Participants
3
Reactant 2
Product 1
Procedure
The procedure of Example 49 is repeated using 0.345 g of tetrahydropapaverine hydrochloride and 0.30 g of α-(5-iodopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile. This affords 0.263 g of the desired product as a yellow oil.
Sources & evidence
- ORD record
- ord-23f532a1cd22442b89262ad838991feb
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05550149
Reaction notes
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