Potassium Iodide → alpha-(3,4-Dimethoxyphenyl)-7-[2-(dimethylamino)ethoxy]-3, 4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

HRID 273991Notes

Reaction equation

HRID 273991 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:31])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45]Cl.[I-].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:32][C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:31][CH2:45][CH2:44][N:43]([CH3:47])[CH3:42])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 10721301alpha-(3,4-Dimethoxvphenyl)-3.4-dihydro-7-hydroxy-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

Product 1

HCID 10770129alpha-(3,4-Dimethoxyphenyl)-7-[2-(dimethylamino)ethoxy]-3, 4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.583 g of α-(3,4-dimethoxyphenyl)-3,4-dihydro-7-hydroxy-6-methoxy-α-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile in 20 mL of N,N-dimethylformamide is added 0.051 g of 60% sodium hydride in oil and the solution stirred for 1 hour. To this solution is added 0.34 g of freshly prepared 2-dimethylaminoethylchloride and 0.60 g of potassium iodide. The solution is stirred at room temperature for 18 hours and then the volatiles are removed at reduced pressure. The residue is dissolved in a minimum amount of ethyl acetate and 5 volumes of diethyl ether is added. This solution is passed through a short pad of hydrous magnesium silicate and the volatiles are removed at reduced pressure. The residue is chromatographed on silica gel using a gradient of diethyl ether to ethyl acetate to methyl alcohol. This afford 0.14 g of the desired product as a clear glass. MS(Hi res):

Workup

  1. stirringThe solution is stirred at room temperature for 18 hours
  2. customthe volatiles are removed at reduced pressure
  3. dissolutionThe residue is dissolved in a minimum amount of ethyl acetate and 5 volumes of diethyl ether
  4. additionis added
  5. customthe volatiles are removed at reduced pressure
  6. customThe residue is chromatographed on silica gel using a gradient of diethyl ether to ethyl acetate to methyl alcohol

Sources & evidence

ORD record
ord-6b2f5515e9334368b1d16763b5aae1c0
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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