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

HRID 22333Notes

Reaction equation

HRID 22333 reaction equation
[CH2:1]([C:5]1[C:6](=[O:23])[O:7][C:8]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][CH2:20][CH2:21]Cl)=[CH:12][C:9]=2[C:10]=1[CH3:11])[CH2:2][CH2:3][CH3:4].[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>O.CC(C)=O.CC(OC)(C)C>[CH2:1]([C:5]1[C:6](=[O:23])[O:7][C:8]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH2:19][CH2:20][CH2:21][N:33]3[CH2:34][CH2:35][N:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:31][CH2:32]3)=[CH:12][C:9]=2[C:10]=1[CH3:11])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 70961-PhenylpiperazineHCID 5460307FumarateHCID 199276663-butyl-6-(3-chloropropoxy)-7-methoxy-4-methyl-2H-1-benzopyran-2-one

Product 1

HCID 199276833-butyl-7-methoxy-4-methyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 72%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Method B (60 h at 50° C.); starting materials: 3-butyl-6-(3-chloropropoxy)-7-methoxy-4-methyl-2H-1-benzopyran-2-one (example 77) and 1-phenylpiperazine; yield 72%; fusion point 130°-131° C. (from isopropanol and TBME). Fumarate: method E; yield 57%; fusion point 205°-208° C. (from acetone and water).

Workup

  1. customMethod B (60 h at 50° C.)

Sources & evidence

ORD record
ord-a33a2527aae14cb2a79b71c37dcaf1c7
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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