1-Methylpiperazine → 3-(4-Methylpiperazin-1-yl)-isoquinoline

HRID 280686Notes

Reaction equation

HRID 280686 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[N:3]=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 6409683-Chloroisoquinoline

Product 1

HCID 130255683-(4-Methylpiperazin-1-yl)-isoquinoline

Procedure

6.5 g of 3-chloroisoquinoline in 30 ml of N-methylpiperazine are boiled under reflux for 48 hours. The reaction mixture is cooled and partitioned between water and toluene, the toluene phase is washed thoroughly with water and, after drying, the solvent is removed in vacuo. The residue is recrystallized from diisopropyl ether, giving 3.8 g of 3-(4-methylpiperazin-1-yl)-isoquinoline, melting point 93°-94° C.; the dihydrochloride decomposes at 255°-257° C.

Workup

  1. temperatureunder reflux for 48 hours
  2. temperatureThe reaction mixture is cooled
  3. custompartitioned between water and toluene
  4. washthe toluene phase is washed thoroughly with water
  5. customafter drying
  6. customthe solvent is removed in vacuo
  7. customThe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3d650421cd954ba593105994acd0db4a
Source dataset
uspto-grants-1986_05
Patent number
US04590273

Reaction notes

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