6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → alpha-(3,4-Dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-gamma-methyl-alpha-[(4-methylphenyl)thio]-2(1H)-isoquino linepentanenitrile

HRID 273982Notes

Reaction equation

HRID 273982 reaction equation
Cl[CH2:2][CH:3]([CH3:26])[CH2:4][C:5]([S:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:6]#[N:7].Cl.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[CH2:36][NH:35][CH2:34][CH2:33]2>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:5]([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)([CH2:4][CH:3]([CH3:26])[CH2:2][N:35]2[CH2:34][CH2:33][C:32]3[C:37](=[CH:38][C:39]([O:40][CH3:41])=[C:30]([O:29][CH3:28])[CH:31]=3)[CH2:36]2)[C:6]#[N:7])[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 19042099HCID 19042099, compound

Product 1

HCID 20094567alpha-(3,4-Dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-gamma-methyl-alpha-[(4-methylphenyl)thio]-2(1H)-isoquino linepentanenitrileYield 17,563.4%

Procedure

The procedure of Example 2 is repeated using 4.0 g of α-(3-chloro-2-methylpropyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 3.5 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. This affords 0,985 g of the desired product as a yellow foam.

Sources & evidence

ORD record
ord-77e0ce66614b4cff85a6c75c9625f1b0
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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