Chloroform → 2,3-dihydro-7-methoxy-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy}cyclopenta[c][1]benzopyran-4(1H)-one

HRID 22347

Reaction equation

HRID 22347 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:20][CH3:21])=[CH:8][C:9]2[O:14][C:13](=[O:15])[C:12]3[CH2:16][CH2:17][CH2:18][C:11]=3[C:10]=2[CH:19]=1.Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(Cl)(Cl)Cl.C([O-])(=O)/C=C/C([O-])=O>CC(C)=O.C(O)C>[CH3:21][O:20][C:7]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]2[CH2:33][CH2:32][N:31]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][CH3:23])[CH2:36][CH2:35]2)=[CH:19][C:10]2[C:11]3[CH2:18][CH2:17][CH2:16][C:12]=3[C:13](=[O:15])[O:14][C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 5460307FumarateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 199276908-(3-chloropropoxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one

Product 1

HCID 199276642,3-dihydro-7-methoxy-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy}cyclopenta[c][1]benzopyran-4(1H)-oneYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Method A (40 h at 50° C.); starting materials: 8-(3-chloropropoxy)-2,3-dihydro-7-methoxy-cyclopenta[c][1]benzopyran-4(1H)-one (example 83) and 1-(2-methoxyphenyl)piperazine hydrochloride; yield 56%; fusion point 177°-178° C. (from chloroform and ethanol). Fumarate: method E; yield 87%; fusion point 173°-174° C. (from acetone).

Workup

  1. customMethod A (40 h at 50° C.)

Sources & evidence

ORD record
ord-1427fd7ffd9d4cf99a055088fcb1a4b2
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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