Triethylamine → Isoquinoline

HRID 638076Notes

Reaction equation

HRID 638076 reaction equation
ClC[C:3]1[C:12]2[C:7](=[CH:8][C:9](OC)=[C:10](OC)[CH:11]=2)[C:6](CC2C=CC(OC)=C(OC)C=2)=[N:5][CH:4]=1.Cl.COC1C=CC(N2CCNCC2)=CC=1.C(N(CC)CC)C>CS(C)=O.O>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=[CH:4][N:5]=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 8405Isoquinoline

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 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-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-5b36d0f3d1ae4de19583233bf81939ad
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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