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

HRID 22353

Reaction equation

HRID 22353 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]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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:31]2[CH2:32][CH2:33][N:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=3)[CH2:29][CH2:30]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 944591-(2-Pyridyl)piperazineHCID 5460307FumarateHCID 199276908-(3-chloropropoxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one

Product 1

HCID 199277042,3-dihydro-7-methoxy-8-{3-[4-(2-pyridinyl)-1-piperazinyl]propoxy}cyclopenta[c][1]benzopyran-4(1H)-oneYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Method B (75 h at 45° C.); starting materials: 8-(3-chloropropoxy)-2,3-dihydro-7-methoxy-cyclopenta[c][1]benzopyran-4(1H)-one (example 83) and 1-(2-pyridinyl)piperazine; yield 68%; fusion point 152°-154° C. (from chloroform and ethanol). Fumarate: method E; yield 96%; fusion point 205°-207° C. (from acetone).

Workup

  1. customMethod B (75 h at 45° C.)

Sources & evidence

ORD record
ord-facc33b8c3164249976e4ffe74c53a33
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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