Triethylamine → Isoquinoline

HRID 638077Notes

Reaction equation

HRID 638077 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.COC1C=CC=CC=1C1CCNCC1.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 5447384-(2-Methoxyphenyl)piperidineHCID 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 5.0 g of 4-chloromethyl-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]isoquinoline, 2.49 g of 4-(2-methoxyphenyl)piperidine, and 2.63 g of triethylamine in 50 ml of dimethylsulfoxide was heated at 80° for one hour under argon and then the cooled solution was diluted with water and extracted with methylene chloride. The organic layer was washed with sodium bicarbonate solution, dried over sodium sulfate, charcoaled, and evaporated to give 7.0 g of 6,7-dimethoxy-1-}(3,4-dimethoxyphenyl)methyl}-4-[[4-(2-methoxyphenyl)-1-piperidinyl)-1-piperidinyl]methyl]isoquinoline as a yellow foam.

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

Sources & evidence

ORD record
ord-e190ecaaa90a465e9ddf8921e5bfd2cc
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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