Isopropanol → 6-ethoxy-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22310

Reaction equation

HRID 22310 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:15][CH2:16][CH2:17][CH2:18]OS(C)(=O)=O)=[CH:6][C:7]2[O:12][C:11](=[O:13])[CH:10]=[CH:9][C:8]=2[CH:14]=1)[CH3:2].[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(C)C.C([O-])(=O)/C=C/C([O-])=O>CC(C)=O.C(O)C>[CH2:1]([O:3][C:4]1[C:5]([O:15][CH2:16][CH2:17][CH2:18][N:33]2[CH2:34][CH2:35][N:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:31][CH2:32]2)=[CH:6][C:7]2[O:12][C:11](=[O:13])[CH:10]=[CH:9][C:8]=2[CH:14]=1)[CH3:2]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 70961-PhenylpiperazineHCID 5460307FumarateHCID 199277406-ethoxy-7-[3-(methanesulfonyloxy)-propoxy]-2H-1-benzopyran-2-one

Product 1

HCID 99532766-ethoxy-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Method B (40 h at 50° C.); starting materials: 6-ethoxy-7-[3-(methanesulfonyloxy)-propoxy]-2H-1-benzopyran-2-one (see example 71) and 1-phenylpiperazine; yield 76%; fusion point 116° to 117° C. (from isopropanol). Fumarate: method E; yield 94%; fusion point 185° to 187° C. (from ethanol and acetone).

Workup

  1. customMethod B (40 h at 50° C.)

Sources & evidence

ORD record
ord-a543d73e1b6b42c99603dc6ee57f91b7
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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