1-(4-Ethylpiperazin-1-yl)-3-(4-methoxyphenyl)isoquinoline → 1-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinoline

HRID 1814441Notes

Reaction equation

HRID 1814441 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]>Br>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

3

Reactant 1

HCID 99501681-(4-Ethylpiperazin-1-yl)-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 1357190421-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinolineYield 75%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-(4-Ethylpiperazin-1-yl)-3-(4-methoxyphenyl)isoquinoline (1.50 g) obtained in Example 10 was dissolved in 48% hydrobromic acid (15 ml) and reacted at 120° C. for 1.5 hr. The reaction solution was evaporated to a final half volume, and ice-cooled. The resulting precipitates were collected by filtration, and then washed with a small amount of ice-cooled water. The precipitates were treated with a 2N aqueous solution of sodium hydroxide, followed by collecting the precipitates by filtration, washed with water and ether/n-hexane, and then dried in warm air, to give the title compound (1.08 g, yield; 75%).

Workup

  1. customreacted at 120° C. for 1.5 hr
  2. customThe reaction solution was evaporated to a final half volume, and ice-
  3. temperaturecooled
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with a small amount of ice-
  7. temperaturecooled water
  8. additionThe precipitates were treated with a 2N aqueous solution of sodium hydroxide
  9. customby collecting the
  10. customprecipitates by filtration
  11. washwashed with water and ether/n-hexane
  12. customdried in warm air

Sources & evidence

ORD record
ord-6df015cfc08f4395b2b080a6922a4e10
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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