Reaction #50607

ord-ee803333f37a47e09dae10cb3370c666

Reaction equation

COc1cc2oc(=O)cc(C(F)(F)F)c2cc1O
6-hydroxy-7-methoxy-4-(trifluoromethyl)-2H-1-benzopyran-2-one
ClCCCN1CCC(c2ccccc2)CC1
1-(3-chloropropyl)-4-phenylpiperidine
O=C([O-])/C=C/C(=O)[O-]
Fumarate
→
COc1cc2oc(=O)cc(C(F)(F)F)c2cc1OCCCN1CCC(c2ccccc2)CC1
7-methoxy-6-[3-(4-phenyl-1-piperidinyl)propoxy]-4-(trifluoromethyl)-2H-1-benzopyran-2-one
Yield 45.0%

Reactants

COc1cc2oc(=O)cc(C(F)(F)F)c2cc1O
6-hydroxy-7-methoxy-4-(trifluoromethyl)-2H-1-benzopyran-2-one
ClCCCN1CCC(c2ccccc2)CC1
1-(3-chloropropyl)-4-phenylpiperidine
O=C([O-])/C=C/C(=O)[O-]
Fumarate

Reagents

None

Solvents

COC(C)(C)C
TBME
CCO
ethanol
CO
methanol
COC(C)(C)C
TBME

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod D (3 h at 85° C.)

Procedure

Method D (3 h at 85° C.); starting materials: 6-hydroxy-7-methoxy-4-(trifluoromethyl)-2H-1-benzopyran-2-one (example 104) and 1-(3-chloropropyl)-4-phenylpiperidine; yield 45%; fusion point 125°-126° C. (from TBME and methanol). Fumarate: method E; yield 59%; fusion point 176°-179° C. (from ethanol and TBME).

Source

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