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

HRID 22352

Reaction equation

HRID 22352 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.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1)([O-:24])=[O:23].C([O-])(=O)/C=C/C([O-])=O>CC(C)=O>[CH3:21][O:20][C:7]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]2[CH2:35][CH2:36][N:31]([C:28]3[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=3)[CH2:32][CH2:33]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

5

Reactant 3

HCID 804471-(4-Nitrophenyl)piperazineHCID 5460307FumarateHCID 199276908-(3-chloropropoxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one

Product 1

HCID 199276682,3-dihydro-7-methoxy-8-{3-[4-(4-nitrophenyl)-1-piperazinyl]propoxy}cyclopenta[c][1]benzopyran-4(1H)-oneYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Method B (60 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-(4-nitrophenyl)piperazine; yield 43%; fusion point 226°-228° C. (decomposes; from acetone). Fumarate: method E; yield 92%; fusion point 216° C. (decomposes; from acetone).

Workup

  1. customMethod B (60 h at 50° C.)

Sources & evidence

ORD record
ord-4fbeac3717a44a1b98fa1cdb5f7bd5dd
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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