Sodium Iodide → 2-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

HRID 863889Notes

Reaction equation

HRID 863889 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.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][NH:33][CH2:32][CH2:31]2.C(N(C(C)C)CC)(C)C.[I-].[Na+]>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[C:35](=[CH:36][CH:37]=[C:28]([O:27][CH3:26])[CH:29]=3)[CH2:34]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 108122034-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

Product 1

HCID 106731562-[6-(3,4-Dimethoxyphenyl)-6-[(4-methylphenyl)thio]-hexyl]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.23 g of 4-[6-bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene in 40 mL of acetonitrile is added 3.88 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, 1.74 mL of diisopropylethylamine and 0.01 g of sodium iodide. The solution is heated to reflux for 43 hours and cooled to room temperature. The reaction mixture is partitioned between chloroform and aqueous potassium carbonate and the organic layer is dried over magnesium sulfate. The volatiles are removed at reduced pressure and the residue chromatographed on silica gel using a gradient elution of hexane to chloroform to methyl alcohol. The residue from the chromatography is dissolved in diethyl ether and passed through diatomaceous earth. This affords 4.4 g of the desired product as a yellow oil. MS(FAB): m/z 506(M+H). Calcd for C31H39NO3S: C=73.62, H=7.77, N=2.77, S=6.34 Found C=73.37, H=7.88, N=2.70, S=6.13

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 43 hours
  3. customThe reaction mixture is partitioned between chloroform and aqueous potassium carbonate
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customThe volatiles are removed at reduced pressure
  6. customthe residue chromatographed on silica gel using
  7. washa gradient elution of hexane to chloroform to methyl alcohol
  8. dissolutionThe residue from the chromatography is dissolved in diethyl ether

Sources & evidence

ORD record
ord-2a3cfa72bbc8483b8f6b9126694324c3
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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