ChemicalBook CAS DataBase List Darifenacin

Darifenacin synthesis

11synthesis methods

Product Name:Darifenacin
CAS Number:133099-04-4
Molecular formula:C28H30N2O2
Molecular Weight:426.55

127264-14-6 Synthesis

127264-14-6
237 suppliers
$6.00/250mg

3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine

134002-25-8
46 suppliers
$306.00/1g

133099-04-4
123 suppliers
$39.00/10mg

Yield:133099-04-4 9%

Reaction Conditions:

with potassium carbonate in acetonitrile for 2 h;Heating / reflux;

Steps:

1.11
(S)-2-{1-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-pyrrolidin-3-yl}-2,2-diphenyl-acetamide: A mixture of 5-(2-bromo-ethyl)-2,3-dihydro-benzofuran (0.065 g, 0.29 mmol), (S)-2,2-diphenyl-2-pyrrolidin-3-yl-acetamide (0.100 g, 0.35 mmol), anhydrous potassium carbonate (0.094 g, 0.67 mmol) and acetonitrile (5 mL) was heated at reflux for about 2 hours. The solvent was distilled off and following standard extractive workup with ethyl acetate, the crude product which was purified by preparative HPLC to yield the title compound as a foam (0.011 g, 9%). ¹H NMR (400 MHz, CDCl₃) δ 1.58-1.80 (m, 2H), 1.99-2.15 (m, 2H), 2.68-3.19 (m, 9H), 3.62 (br, 1H), 4.53 (t, J=8.5 Hz, 2H), 5.44 (br, 1H), 6.67 (d, J=8.0 Hz, 1H), 6.86 (d, J=7.7 Hz, 1H), 6.99 (s, 1H), 7.20-7.40 (m, 10H); MS 427 (M+1).

References:

AUSPEX PHARMACEUTICALS, INC. US2009/5431, 2009, A1 Location in patent:Page/Page column 33

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133033-99-5 Synthesis