6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → alpha-(3,4-Dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy alpha-[(4-methylphenyl)thio]-2(1H)-isoquinoline tridecanenitrile
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([S:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[C:14]#[N:15].Cl.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[CH2:43][NH:42][CH2:41][CH2:40]2>>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([C:13]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:42]2[CH2:41][CH2:40][C:39]3[C:44](=[CH:45][C:46]([O:47][CH3:48])=[C:37]([O:36][CH3:35])[CH:38]=3)[CH2:43]2)[C:14]#[N:15])[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]Participants
3
Reactant 2
Product 1
Procedure
The procedure of Example 3 is repeated using 3.14 g of α-(11-bromoundecyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.03 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. This affords 2.2 g of the desired product as a light yellow oil. MS(Hi res): m/z Calcd for C39H52N2O4S 644.3648 Found 645.3730(M+H). Calcd for C39H52N2O4S 1/2H2O: C=71.63, H=8.17, N=4.29, S=4.90 Found C=71.31, H=8.19, N=4.10, S=4.71
Sources & evidence
- ORD record
- ord-40ec51b6bce54acda72e20f80f28c344
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561141
Reaction notes
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