5,6,7,8-Tetrahydro-1,3-dioxolo(4,5-g)isoquinoline → 6-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline

HRID 863890Notes

Reaction equation

HRID 863890 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.[CH2:26]1[O:38][C:37]2[CH:36]=[C:35]3[C:30]([CH2:31][CH2:32][NH:33][CH2:34]3)=[CH:29][C:28]=2[O:27]1>C(#N)C>[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:33]2[CH2:32][CH2:31][C:30]3[CH:29]=[C:28]4[O:27][CH2:26][O:38][C:37]4=[CH:36][C:35]=3[CH2:34]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 270135,6,7,8-Tetrahydro-1,3-dioxolo(4,5-g)isoquinolineHCID 108122034-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

Product 1

HCID 105778646-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 46 is repeated using 3.67 g of 4-[6-bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene in 40 mL of acetonitrile and 2.65 g of 6,7-methylenedioxy-1,2,3,4-tetrahydroiso quinoline. This affords 4.13 g of the desired product as a yellow gum. MS(CI): m/z 520(M+H+). Calcd for C31H37NO4S 7/8H2O: C=69.53, H=7.15, N=2.57, S=5.84 Found C=69.54, H=7.30, N=2.62, S=5.98

Sources & evidence

ORD record
ord-0c38e48f87704fbc911d8a3a12e46dcd
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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