ChemicalBook CAS DataBase List Flecainide

Flecainide synthesis

1synthesis methods

Product Name:Flecainide
CAS Number:54143-55-4
Molecular formula:C17H20F6N2O3
Molecular Weight:414.34

Flecainide, N-(2-piperidylmethyl)-2,5-bis-(2,2,2-trifluoroethoxy)benzamide (18.1.14), is synthesized from 2,5-dihydroxybenzoic acid. Reacting this with trifluoroethylfluoromethylsulfonate gives 2.2.2-trifluoroethoxylation of all three hydroxyl groups, to produce 2,2,2-trifluoroethyl ester of 2,5-bis-(2,2,2-trifluoroethoxy)benzoic acid (18.1.12). Reacting this with 2-aminomethylpiridine gives the corresponding amide (18.1.13), which upon reduction of the pyridine ring with hydrogen gives flecainide (18.1.14).

22990-77-8 Synthesis

22990-77-8
221 suppliers
$27.00/5g

35480-31-0 Synthesis

METHYL 2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZOATE

35480-31-0
49 suppliers
$19.00/1g

54143-55-4
113 suppliers
$46.00/10mg

Yield:54143-55-4 85%

Reaction Conditions:

in toluene for 10 h;Heating / reflux;

Steps:

5 Preparation of Flecainide
;A mixture of methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate (1.5 g), 2-(aminomethyl)piperidine (0.62 g) in toluene (3 ml) was stirred at reflux for 10 hours. After cooling to room temperature, water (10 ml) was added and two layers solution were separated. The aqueous layer was extracted with toluene (2*10 ml) and the combined organic layers were washed with water (3*10 ml). The organic layer was concentrated under reduced pressure to give Flecainide free base as a white solid (1.63 g, 85%).

References:

Wang, Zhi-Xian;Li, Yuanqiang;Guntoori, Bhaskar Reddy US2005/59825, 2005, A1 Location in patent:Page/Page column 4-5

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