Diethyl Ether → {1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol

A solution of 1N ZnCl2 in Et2O (182 mL, 182 mmol) was added to a solution of 4-(hydroxymethyl)-1-piperidinecarbonitrile (21.3 g, 152 mmol) and N-hydroxy-2-methylpropanimidamide (18.6 g, 182 mmol) in EtOAc (50 mL) at ambient temperature. The reaction mixture was left at ambient temperature for 30 min, decanted, and was treated with concentrated HCl (45 mL) and ethanol 20 mL). The mixture was heated at reflux for 2 h. The mixture was evaporated to dryness, and the resulting residue was charged with water and the pH was adjusted to basic with K2CO3. The mixture was extracted with EtOAc and the material obtained was combined with 9 other batches prepared similarly and purified by silica gel chromatography to give 150 g of {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol.

1. customdecanted
2. additionwas treated with concentrated HCl (45 mL) and ethanol 20 mL)
3. temperatureThe mixture was heated
4. temperatureat reflux for 2 h
5. customThe mixture was evaporated to dryness
6. additionthe resulting residue was charged with water
7. extractionThe mixture was extracted with EtOAc
8. customthe material obtained
9. customprepared similarly
10. custompurified by silica gel chromatography

ORD-Eintrag

ord-132c494bbfdd4826bd3d9099cd03ce51

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101634B2