Reaction #50589

ord-bdf7ae22919d4084bdf3473889aeac55

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CS(=O)(=O)OCCCOc1cc2oc(=O)ccc2cc1OC1CCCC1
6-(cyclo-pentyloxy)-7-[3-(methanesulfonyloxy)propoxy]-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME
→
O=c1ccc2cc(OC3CCCC3)c(OCCCN3CCN(c4ccccc4)CC3)cc2o1
6-(cyclopentyloxy)-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 68.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CS(=O)(=O)OCCCOc1cc2oc(=O)ccc2cc1OC1CCCC1
6-(cyclo-pentyloxy)-7-[3-(methanesulfonyloxy)propoxy]-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME

Reagents

None

Solvents

CC(C)O
isopropanol
CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (25 h at 40° C.)

Procedure

Method B (25 h at 40° C.); starting materials: 6-(cyclo-pentyloxy)-7-[3-(methanesulfonyloxy)propoxy]-2H-1-benzopyran-2-one (example 72) and 1-phenylpiperazine; yield 68%; fusion point 101°-103° C. (from TBME and isopropanol). Fumarate: method E; yield 88%; fusion point 171°-173° C. (from acetone).

Source

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