Reaction #50614

ord-06983b3b92bb4e458a75cae28a70b5ba

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)c3c(c2cc1OCCCOS(C)(=O)=O)CCCC3
7,8,9,10-tetrahydro-2-[3-(methanesulfonyloxy)propoxy]-3-methoxy-6H-dibenzo[b,d]pyran-6-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME
→
COc1cc2oc(=O)c3c(c2cc1OCCCN1CCN(c2ccccc2)CC1)CCCC3
7,8,9,10-tetrahydro-3-methoxy-2-[3-(4-phenyl-1-piperazinyl)propoxy]-6H-dibenzo[b,d]pyran-6-one
Yield 94.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)c3c(c2cc1OCCCOS(C)(=O)=O)CCCC3
7,8,9,10-tetrahydro-2-[3-(methanesulfonyloxy)propoxy]-3-methoxy-6H-dibenzo[b,d]pyran-6-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
COC(C)(C)C
TBME

Reagents

None

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (24 h at 60° C.)

Procedure

Method B (24 h at 60° C.); starting materials: 7,8,9,10-tetrahydro-2-[3-(methanesulfonyloxy)propoxy]-3-methoxy-6H-dibenzo[b,d]pyran-6-one (example 80) and 1-phenylpiperazine; yield 94%; fusion point 104°-106° C. (from TBME and isopropanol). Fumarate: method E; yield 92%; fusion point 160°-161° C. (from ethanol and acetone).

Source

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