Potassium Carbonate → HCID 22503186, compound

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

Reactant 4

HCID 11430Potassium Carbonate

HCID 24813Phosphorus oxychloride

HCID 791961-Ethylpiperazine

HCID 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.