1-(2-Methoxyphenyl)piperazine → isoquinolin-N-oxide

HRID 638081

Reaction equation

HRID 638081 reaction equation
COC1C=C(C=CC=1OC)C[C:7]1[C:16]2[C:11](=[CH:12][C:13](OC)=[C:14](OC)[CH:15]=2)[CH:10]=[CH:9][N+:8]=1[O-:21].CN(C)C=O.COC1C=CC=CC=1N1CCNCC1>C(N(CC)CC)C>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N+:8]=1[O-:21]

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6228DimethylformamideHCID 11810396AGN-PC-00GMS2

Product 1

HCID 290378isoquinolin-N-oxide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2.5g 4-chloromethyl-1-(3,4-dimethoxybenzyl-6,7-dimethoxyisoquinoline 2-oxide, 35 ml dimethylformamide, 1.8 triethylamine and 1.29 g 1-(2-methoxyphenyl)piperazine was stirred and heated under nitrogen at 50° for 7 hours. After evaporation of the solvent, the residue was partitioned between methylene chloride and water. The methylene chloride solution was washed with water and dried. After removal of the solvent in vacuo, the residue (3.5 g) was crystallized from methylene chloride/ethyl acetate to yield 3.05 g of yellow, hygroscopic crystals of 1-(3,4)-dimethoxybenzyl)-6,7-dimethoxy-4-{]4'-(2-methoxyphenyl)-1'-piperazinyl]methyl} isoquinoline 2-oxide, mp 128°-129° (dec.).

Workup

  1. temperatureheated under nitrogen at 50° for 7 hours
  2. customAfter evaporation of the solvent
  3. customthe residue was partitioned between methylene chloride and water
  4. washThe methylene chloride solution was washed with water
  5. customdried
  6. customAfter removal of the solvent in vacuo
  7. customthe residue (3.5 g) was crystallized from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-a7652a369f1c41c3a08384f1bf64b0d4
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Linked notes

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