Reaction #50586

ord-6847489470b44f3c997251298a9f7a2a

Reaction equation

COc1ccc2oc(=O)c(OCCCCl)cc2c1
3-(chloropropoxy)-6-methoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
O=C([O-])/C=C/C(=O)[O-]
Fumarate
→
COc1cc2ccc(=O)oc2cc1OCCCN1CCN(c2ccccc2)CC1
6-methoxy-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 94.0%

Reactants

COc1ccc2oc(=O)c(OCCCCl)cc2c1
3-(chloropropoxy)-6-methoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
O=C([O-])/C=C/C(=O)[O-]
Fumarate

Reagents

None

Solvents

COC(C)(C)C
TBME
CC(C)O
isopropanol
COC(C)(C)C
TBME
CC(C)O
isopropanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (9 h at 70° C.)

Procedure

Method B (9 h at 70° C.); starting materials: 7-[3-(chloropropoxy)-6-methoxy-2H-1-benzopyran-2-one (see example 69) and 1-phenylpiperazine; yield 94%; fusion point 82° to 83° (from isopropanol and TBME). Fumarate: method E; yield 94%; fusion point 168° to 170° C. (from isopropanol and TBME).

Source

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