Reaction #50602

ord-59e6ac6dded24aa182cf6bb832ef04bd

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)cc(C)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CC(C)O
isopropanol
→
COc1cc2oc(=O)cc(C)c2cc1OCCCN1CCN(c2ccccc2)CC1
7-methoxy-4-methyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 77.0%

Reactants

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

Reagents

None

Solvents

CC(C)=O
acetone
CCO
ethanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (32 h at 50° C.)

Procedure

Method B (32 h at 50° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one (example 74) and 1-phenylpiperazine; yield 77%; fusion point 137°-140° C. (from isopropanol and ethanol). Fumarate: method E; yield 79%; fusion point 195°-200° C. (from ethanol and acetone).

Source

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