Reaction #50608

ord-f6916d529fe9473aa2dc8d74fbd0b5a2

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COC(C)(C)C
TBME
CCCc1cc(=O)oc2cc(OC)c(OCCCOS(C)(=O)=O)cc12
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-propyl-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine
→
CCCc1cc(=O)oc2cc(OC)c(OCCCN3CCC(c4ccccc4)CC3)cc12
7-methoxy-6-[3-(4-phenyl-1-piperidinyl)propoxy]-4-propyl-2H-1-benzopyran-2-one
Yield 54.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
COC(C)(C)C
TBME
CCCc1cc(=O)oc2cc(OC)c(OCCCOS(C)(=O)=O)cc12
6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-propyl-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine

Reagents

None

Solvents

—
petroleum ether
CO
methanol
CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod A (20 h at 60° C.)

Procedure

Method A (20 h at 60° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-propyl-2H-1-benzopyran-2-one (example 76) and 4-phenylpiperidine; yield 54%; fusion point 101°-102° C. (from TBME and petroleum ether). Fumarate: method E; yield 62%; fusion point 191°-194° C. (from acetone and methanol).

Source

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