Reaction #50604

ord-f564062cc0f5453c9b0243e591b2ff3c

Reaction equation

COc1cc2oc(=O)c(C)c(C)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
O=C([O-])/C=C/C(=O)[O-]
Fumarate
→
COc1cc2oc(=O)c(C)c(C)c2cc1OCCCN1CCN(c2ccccc2)CC1
7-methoxy-3,4-dimethyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 64.0%

Reactants

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

Reagents

None

Solvents

CO
methanol
CCO
ethanol
CO
methanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod A (45 h at 50° C.)

Procedure

Method A (45 h at 50° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one (example 75) and 1-phenylpiperazine; yield 64%; fusion point 151°-152° C. (from ethanol and methanol). Fumarate (×0.5 C4H4O4): method E; yield 92%; fusion point 207°-209° C. (from ethanol and methanol).

Source

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