Reaction #50618

ord-a18af3b2d2b641faa36d78b3a98b6f22

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)c3c(c2cc1OCCCCCBr)CCC3
8-(5-bromopentyloxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CC(C)O
isopropanol
CC(C)O
isopropanol
→
COc1cc2oc(=O)c3c(c2cc1OCCCCCN1CCN(c2ccccc2)CC1)CCC3
2,3-dihydro-7-methoxy-8-[5-(4-phenyl-1-piperazinyl)pentyloxy]cyclopenta[c][1]benzopyran-4(1H)-one
Yield 97.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)c3c(c2cc1OCCCCCBr)CCC3
8-(5-bromopentyloxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CC(C)O
isopropanol
CC(C)O
isopropanol

Reagents

None

Solvents

COC(C)(C)C
TBME

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (10 h at 80° C.)

Procedure

Method B (10 h at 80° C.); starting materials: 8-(5-bromopentyloxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one (example 85) and 1-phenylpiperazine; yield 97%; fusion point 118°-120° C. (from isopropanol). Fumarate (x 0.5 C4H4O4): method E; yield 93%; fusion point 153°-155° C. (from isopropanol and TBME).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428038uspto-grants-1995_06