Reaction #50603

ord-139cda73f5df4923b379b1bd496e259a

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)cc(C)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine
CC(C)O
isopropanol
→
COc1cc2oc(=O)cc(C)c2cc1OCCCN1CCC(c2ccccc2)CC1
7-methoxy-4-methyl-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one
Yield 77.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COc1cc2oc(=O)cc(C)c2cc1OCCCOS(C)(=O)=O
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine
CC(C)O
isopropanol

Reagents

None

Solvents

CCO
ethanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (26 h at 50° C.)

Procedure

Method B (26 h at 50° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one (example 74) and 4-phenylpiperidine; yield 77%; fusion point 141°-143° C. (from isopropanol and ethanol). Fumarate: method E; yield 89%; fusion point 221°-223° C. (from ethanol).

Source

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