Triethylamine → 6,7-Dimethoxy-1-{(3,4-dimethoxyphenyl)methyl}-4-([4-(4-methoxyphenyl)-1-piperazinyl]methyl)isoquinoline

HRID 463717Notes

Reaction equation

HRID 463717 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.Cl.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=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:40]1[CH2:41][CH2:42][N:37]([C:34]2[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:36][CH:35]=2)[CH2:38][CH2:39]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122011971-(4-Methoxyphenyl)piperazine hydrochlorideHCID 135605294-Chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline

Product 1

HCID 135605376,7-Dimethoxy-1-{(3,4-dimethoxyphenyl)methyl}-4-([4-(4-methoxyphenyl)-1-piperazinyl]methyl)isoquinolineYield 80%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1.16 g of 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline, 0.8 g of 1-(para-methoxyphenyl)piperazine hydrochloride, and 1.3 ml of triethylamine in 10 ml 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 1.3 g of 6,7-dimethoxy-1-{(3,4-dimethoxyphenyl)methyl}-4-([4-(4-methoxyphenyl)-1-piperazinyl]methyl)isoquinoline as a yellow solid, mp 176°-177°. Recrystallization from ethanol provided the analytical sample, mp 176°-177°.

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-597f3e93e48f4a689ce84fa0b039ec55
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

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