Reaction #50611

ord-a33a2527aae14cb2a79b71c37dcaf1c7

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CCCCc1c(C)c2cc(OCCCCl)c(OC)cc2oc1=O
3-butyl-6-(3-chloropropoxy)-7-methoxy-4-methyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CC(C)O
isopropanol
→
CCCCc1c(C)c2cc(OCCCN3CCN(c4ccccc4)CC3)c(OC)cc2oc1=O
3-butyl-7-methoxy-4-methyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one
Yield 72.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CCCCc1c(C)c2cc(OCCCCl)c(OC)cc2oc1=O
3-butyl-6-(3-chloropropoxy)-7-methoxy-4-methyl-2H-1-benzopyran-2-one
c1ccc(N2CCNCC2)cc1
1-phenylpiperazine
CC(C)O
isopropanol

Reagents

None

Solvents

O
water
CC(C)=O
acetone
COC(C)(C)C
TBME

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (60 h at 50° C.)

Procedure

Method B (60 h at 50° C.); starting materials: 3-butyl-6-(3-chloropropoxy)-7-methoxy-4-methyl-2H-1-benzopyran-2-one (example 77) and 1-phenylpiperazine; yield 72%; fusion point 130°-131° C. (from isopropanol and TBME). Fumarate: method E; yield 57%; fusion point 205°-208° C. (from acetone and water).

Source

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