Reaction #50587

ord-d60a35bd97fd4ef6ac58e78b0a9da410

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CCOc1cc2oc(=O)ccc2cc1OCCCCl
6-(3-chloropropoxy)-7-ethoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CO
methanol
→
CCOc1cc2oc(=O)ccc2cc1OCCCN1CCN(c2ccccc2)CC1
7-ethoxy-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 57.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CCOc1cc2oc(=O)ccc2cc1OCCCCl
6-(3-chloropropoxy)-7-ethoxy-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CO
methanol

Reagents

None

Solvents

CCO
ethanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod A (26 h at 60° C.)

Procedure

Method A (26 h at 60° C.); starting materials: 6-(3-chloropropoxy)-7-ethoxy-2H-1-benzopyran-2-one (see example 70) and 1-phenylpiperazine; yield 57%; fusion point 151° to 153° (from methanol and ethanol). Fumarate: method E; yield 78%; fusion point 170° to 173° C. (from ethanol).

Source

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