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

HRID 22311

Reaction equation

HRID 22311 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([O:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:9][C:10]3[O:15][C:14](=[O:16])[CH:13]=[CH:12][C:11]=3[CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC(OC)(C)C.C([O-])(=O)/C=C/C([O-])=O>CC(C)=O.C(O)(C)C>[CH:1]1([O:6][C:7]2[C:8]([O:18][CH2:19][CH2:20][CH2:21][N:36]3[CH2:37][CH2:38][N:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:34][CH2:35]3)=[CH:9][C:10]3[O:15][C:14](=[O:16])[CH:13]=[CH:12][C:11]=3[CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 15413tert-Butyl methyl etherHCID 5460307FumarateHCID 199276356-(cyclo-pentyloxy)-7-[3-(methanesulfonyloxy)propoxy]-2H-1-benzopyran-2-one

Product 1

HCID 199276396-(cyclopentyloxy)-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Method B (25 h at 40° C.); starting materials: 6-(cyclo-pentyloxy)-7-[3-(methanesulfonyloxy)propoxy]-2H-1-benzopyran-2-one (example 72) and 1-phenylpiperazine; yield 68%; fusion point 101°-103° C. (from TBME and isopropanol). Fumarate: method E; yield 88%; fusion point 171°-173° C. (from acetone).

Workup

  1. customMethod B (25 h at 40° C.)

Sources & evidence

ORD record
ord-bdf7ae22919d4084bdf3473889aeac55
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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