Triphenylphosphine → 5-[(1-Methyl-4-piperidinyl)oxy]-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Temperatur

115 °C

A solution of DIAD (0.30 ml, 1.56 mmol) in toluene (1 ml) was added dropwise to a solution of 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 29; 200 mg, 0.624 mmol), 1-methyl-4-piperidinol (79 mg, 0.687 mmol) and Ph3P (409 mg, 1.561 mmol) in toluene under nitrogen at 0° C. The reaction mixture was stirred at 115° C. overnight. The mixture was then cooled and concentrated. The residue was added to water and extracted with ethyl acetate (3×60 ml). The organic phase was washed with saturated brine (30 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product. The crude product was purified by Pre-TCL (DCM:methanol=8:1) to yield the title compound as a yellow solid. 36 mg.

1. temperatureThe mixture was then cooled
2. concentrationconcentrated
3. additionThe residue was added to water
4. extractionextracted with ethyl acetate (3×60 ml)
5. washThe organic phase was washed with saturated brine (30 ml)
6. dry with materialdried over sodium sulphate
7. customevaporated in vacuo
8. customto give the crude product
9. customThe crude product was purified by Pre-TCL (DCM:methanol=8:1)

ORD-Eintrag

ord-5a81a0a6744744b895401e240d469f09

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08778939B2