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

HRID 863880Notes

Reaction equation

HRID 863880 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): m/z Calcd for C36H47N3O4S 617.3287 Found 617.3302

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-209c5ba6fd664232b82b79801fde39ed
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

Loading…