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

HRID 1078741Notes

Reaction equation

HRID 1078741 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

HCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 10673824alpha-(11-Bromoundecyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile

Product 1

HCID 10675684alpha-(3,4-Dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy alpha-[(4-methylphenyl)thio]-2(1H)-isoquinoline tridecanenitrileYield 57.9%

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.

Sources & evidence

ORD record
ord-fd829e8731c64051bd60d5a4e5fa4de3
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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