Reaction #50585

ord-4e9e7528c2ef4b708c884f4ab638ad29

Reaction equation

COc1cc2oc(=O)ccc2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
O=C([O-])/C=C/C(=O)[O-]
Fumarate
→
COc1cc2oc(=O)ccc2cc1OCCCN1CCN(c2ccccc2)CC1
7-methoxy-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 55.0%

Reactants

COc1cc2oc(=O)ccc2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
O=C([O-])/C=C/C(=O)[O-]
Fumarate

Reagents

None

Solvents

CCO
ethanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod A (23 h at 60° C.)

Procedure

Method A (23 h at 60° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-2H-1-benzopyran-2-one (see example 67) and 1-phenylpiperazine; yield 55%; fusion point 124° to 125° C. (from ethanol). Fumarate: method E; yield 88%; fusion point 172° to 173° C. (from ethanol).

Source

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