1-Phenylpiperazine → 7,8,9,10-tetrahydro-3-methoxy-2-[3-(4-phenyl-1-piperazinyl)propoxy]-6H-dibenzo[b,d]pyran-6-one

HRID 22336Notes

Reaction equation

HRID 22336 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:24]([O:25][CH3:26])=[CH:23][C:13]2[O:14][C:15](=[O:22])[C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:12]=2[CH:11]=1)(=O)=O.[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(O)(C)C>[CH3:26][O:25][C:24]1[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:36]2[CH2:37][CH2:38][N:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:34][CH2:35]2)=[CH:11][C:12]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[C:15](=[O:22])[O:14][C:13]=2[CH:23]=1

Participants

8

Reactant 4

HCID 70961-PhenylpiperazineHCID 15413tert-Butyl methyl etherHCID 5460307FumarateHCID 199277097,8,9,10-tetrahydro-2-[3-(methanesulfonyloxy)propoxy]-3-methoxy-6H-dibenzo[b,d]pyran-6-one

Product 1

HCID 199276377,8,9,10-tetrahydro-3-methoxy-2-[3-(4-phenyl-1-piperazinyl)propoxy]-6H-dibenzo[b,d]pyran-6-oneYield 94%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

Method B (24 h at 60° C.); starting materials: 7,8,9,10-tetrahydro-2-[3-(methanesulfonyloxy)propoxy]-3-methoxy-6H-dibenzo[b,d]pyran-6-one (example 80) and 1-phenylpiperazine; yield 94%; fusion point 104°-106° C. (from TBME and isopropanol). Fumarate: method E; yield 92%; fusion point 160°-161° C. (from ethanol and acetone).

Workup

  1. customMethod B (24 h at 60° C.)

Sources & evidence

ORD record
ord-06983b3b92bb4e458a75cae28a70b5ba
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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