1-(2-Methoxyphenyl)piperazine → Elziverine

HRID 638075Notes

Reaction equation

HRID 638075 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[N:5][CH:4]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N(CC)CC)C>CS(C)=O.O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH3:16])[C:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)=[N:5][CH:4]=[C:3]2[CH2:2][N:39]1[CH2:40][CH2:41][N:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[O:29][CH3:28])[CH2:37][CH2:38]1

Participants

6

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 135605294-Chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline

Product 1

HCID 65839ElziverineYield 79.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 10.0 g of 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline, 5.5 g of 1-(2-methoxyphenyl)piperazine, and 7.6 ml of triethylamine in 100 ml of dimethylsulfoxide was heated at 80° for one hour under argon. The cooled solution was then diluted with water and extracted with methylene chloride. The organic layer was washed with sodium bicarbonate solution, dried over sodium sulfate, charcoaled, and evaporated. The residue was crystallized from ethanol to give 11.1 g of 6,7-dimethoxy-1-{(3,4-dimethoxyphenyl)methyl}-4-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]isoquinoline as a yellow solid, mp 117°-119°.

Workup

  1. temperaturewas heated at 80° for one hour under argon
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-aa2499f728314c3a93f147aee40a42d0
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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