6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-alpha-((4-methylphenyl)thio)-2(1H)-isoquinolineheptanenitrile

HRID 863873Notes

Reaction equation

HRID 863873 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].[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>>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:7]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:6][CH2:5][CH2:4][CH2:3][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:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

3

Reactant 2

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 10573255alpha-(5-Chloropentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)-thio]benzeneacetonitrile

Product 1

HCID 9829281alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-alpha-((4-methylphenyl)thio)-2(1H)-isoquinolineheptanenitrileYield 56.9%

Procedure

The procedure of Example 3 is repeated using 4.65 g of α-(5-chloropentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 4.25 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline. This affords 3.67 g of the desired product as a light brown gum. MS(Hi res): m/z Calcd for C33H40N2O4S 0.5H2O 560.2209 Found 561.2287(M+H). Calcd for C33H40N2O4S 0.5H2O: C=69.77, H=7.17, N=4.58, S=5.33 Found C=69.56, H=7.25, N=4.92, S=5.63

Sources & evidence

ORD record
ord-c77da74771374ea19ad13f79e432b7b0
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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