Water → N-(2-diisopropylaminoethyl)-6,7-dimethoxy-N-methyl-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide

HRID 1414286Notes

Reaction equation

HRID 1414286 reaction equation
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[CH2:5][CH2:6][NH:7][C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=2)[CH:11]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:9])([CH3:3])[CH3:2].[H-].[Na+].[CH3:35]I.O>CS(C)=O>[CH:30]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][N:7]([CH3:35])[C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=2)[CH:11]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:9])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21487005HCID 21487005, compound

Product 1

HCID 21486995N-(2-diisopropylaminoethyl)-6,7-dimethoxy-N-methyl-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.4 Parts of N-(2-diisopropylaminoethyl)-6,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide is dissolved in 110 parts of dimethylsulfoxide. Then 0.24 part of sodium hydride, as a 56% suspension in mineral oil, is added. The mixture is stirred for 30 minutes at room temperature. 1.42 Parts of methyl iodide is added portionwise at room temperature and the resultant mixture is stirred overnight in a nitrogen atmosphere. The mixture is then poured into water and extracted with methylene chloride. The methylene chloride extract is dried over anhydrous calcium sulfate and stripped under reduced pressure to give N-(2-diisopropylaminoethyl)-6,7-dimethoxy-N-methyl-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. dry with materialis dried over anhydrous calcium sulfate

Sources & evidence

ORD record
ord-77e50fc122024968946a26db0bbc0f88
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

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