6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline

HRID 863892Notes

Reaction equation

HRID 863892 reaction equation
Br[CH:2]([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[S:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.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>>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:26][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)[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 190420934-[6-Bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene

Product 1

HCID 107927462-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolineYield 38%

Procedure

The procedure of Example 49 is repeated using 5.22 g of 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. This affords 2.49 g of the desired product as a yellow gum. MS(HI res): m/z Calcd for C33H43NO4S 549.29126 Found 549.291 Calcd for C33H43NO4S H2O C=69.81, H=7.99, N=2.47, S=5.64 Found C=70.19, H=7.83, N=2.41, S=5.70

Sources & evidence

ORD record
ord-20b1bd0fdb6c4517a6a1d6405925e644
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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