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

HRID 22334Notes

Reaction equation

HRID 22334 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:27][CH3:28])=[CH:12][C:13]2[O:18][C:17](=[O:19])[CH:16]=[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]=2[CH:26]=1)(=O)=O.[C:29]1([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(OC)(C)C.C([O-])(=O)/C=C/C([O-])=O>C(OCC)C.CC(C)=O.C(O)(C)C>[CH3:28][O:27][C:11]1[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:38]2[CH2:39][CH2:40][N:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:36][CH2:37]2)=[CH:26][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][C:17](=[O:19])[O:18][C:13]=2[CH:12]=1

Participants

8

Reactant 4

HCID 70961-PhenylpiperazineHCID 15413tert-Butyl methyl etherHCID 5460307FumarateHCID 199277316-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-phenyl-2H-1-benzopyran-2-one

Product 1

HCID 199276607-methoxy-4-phenyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 86%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

Method B (60 h at 60° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-phenyl-2H-1-benzopyran-2-one (example 78) and 1-phenylpiperazine; yield 86%; fusion point 139°-141° C. (from TBME and isopropanol). Fumarate: method E; yield 93%; fusion point 145°-147° C. (from acetone and diethylether).

Workup

  1. customMethod B (60 h at 60° C.)

Sources & evidence

ORD record
ord-a08790196abb44409d3a618f7872e071
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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