Reaction #50612

ord-a08790196abb44409d3a618f7872e071

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)cc(-c3ccccc3)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-phenyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME
→
COc1cc2oc(=O)cc(-c3ccccc3)c2cc1OCCCN1CCN(c2ccccc2)CC1
7-methoxy-4-phenyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 86.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)cc(-c3ccccc3)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-phenyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME

Reagents

None

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (60 h at 60° C.)

Procedure

Method B (60 h at 60° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-phenyl-2H-1-benzopyran-2-one (example 78) and 1-phenylpiperazine; yield 86%; fusion point 139°-141° C. (from TBME and isopropanol). Fumarate: method E; yield 93%; fusion point 145°-147° C. (from acetone and diethylether).

Source

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