Potassium Carbonate → HCID 22503186, compound

HRID 1007032Notes

Reaction equation

HRID 1007032 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:19][C:20](=O)[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14]([O:29][CH3:30])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH3:32].C(=O)([O-])[O-].[K+].[K+].P(Cl)(Cl)([Cl:47])=O>>[ClH:47].[CH2:31]([N:33]1[CH2:38][CH2:37][N:36]([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:27]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:13][C:14]=3[O:29][CH3:30])[N:19]=2)[CH2:35][CH2:34]1)[CH3:32]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 791961-EthylpiperazineHCID 22503579HCID 22503579, compound

Product 1

HCID 22503186HCID 22503186, compound

Procedure

The resulting 3-[4-(2-benzyloxyethoxy)-2-methoxyphenyl]isoquinolin-1-one (0.47 g) was added to phosphorus oxychloride (10 ml), and the mixture was reacted at room temperature overnight. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water, an aqueous solution of sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting 1-chloro-3-[4-(2-benzyloxyethoxy)-2-methoxyphenyl]isoquinoline was reacted as it was with N-ethylpiperazine (5 ml) in the presence of potassium carbonate (1.2 g) at 120° C. for 24 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system), to give 1-(4-ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethoxy)-2-methoxyphenyl]isoquinolinehydrochloride (0.11 g) as a yellow powder.

Workup

  1. customthe mixture was reacted at room temperature overnight
  2. customThe reaction solution was evaporated
  3. additionto the resulting residue were added ethyl acetate
  4. custompurified water
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialan aqueous solution of sodium bicarbonate and brine, and dried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting 1-chloro-3-[4-(2-benzyloxyethoxy)-2-methoxyphenyl]isoquinoline was reacted as it
  9. customThe reaction solution was evaporated
  10. additionto the resulting residue were added ethyl acetate
  11. custompurified water
  12. washThe ethyl acetate layer was washed with water and brine
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was evaporated
  15. customthe resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-47e17ea9c69f4769bf355d89afa8b115
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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