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

HRID 863885Notes

Reaction equation

HRID 863885 reaction equation
Br[CH2:2][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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[CH2:35][NH:34][CH2:33][CH2:32]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][N:34]2[CH2:33][CH2:32][C:31]3[C:36](=[CH:37][C:38]([O:39][CH3:40])=[C:29]([O:28][CH3:27])[CH:30]=3)[CH2:35]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 108122034-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

Product 1

HCID 107686862-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]hexyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolineYield 59.6%

Procedure

The procedure of Example 39 is repeated using 2.12 g of 4-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene and 2.3 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride. This affords 1.6 g of the desired product as a light yellow oil. MS(Hi res): m/z Calcd for C32H41NO4S 535.2756 Found 536.2834(M+H). Calcd for C32H41NO4S: C=70.13, H=7.83, N=3.07, S=5.62 Found C=70.15, H=7.51, N=2.79, S=5.25

Sources & evidence

ORD record
ord-43be8ad96fc64fb9bca86c0e10898101
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

Loading…