Reaction #50610

ord-13dfe9d867b84ecfb63a521715149af8

Reaction equation

COc1cc2oc(=O)cc(C(C)C)c2cc1O
6-hydroxy-7-methoxy-4-(1-methylethyl)-2H-1-benzopyran-2-one
ClCCCN1CCC(c2ccccc2)CC1
1-(3-chloropropyl)-4-phenyl-piperidine
O=C([O-])/C=C/C(=O)[O-]
Fumarate
→
COc1cc2oc(=O)cc(C(C)C)c2cc1OCCCN1CCC(c2ccccc2)CC1
7-methoxy-4-(1-methylethyl)-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one
Yield 85.0%

Reactants

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

Reagents

None

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod D (2.5 h at 85° C.)
  2. 2
    Otherfusion point 155°-157° C.

Procedure

Method D (2.5 h at 85° C.); starting materials: 6-hydroxy-7-methoxy-4-(1-methylethyl)-2H-1-benzopyran-2-one (example 105) and 1-(3-chloropropyl)-4-phenyl-piperidine; yield 85%; fusion point 62°-65° C. (from TBME). Fumarate: method E; yield 65%; fusion point 155°-157° C. (from acetone, boiled out with TBME).

Source

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