Water → (1-Isopropylpiperidin-4-yl)methanamine

To a suspension of 10.0 g of LAN in 500 mL of dry THF, at room temperature, was added portionwise 39.7 g of 1-isopropylpiperidine-4-carboxamide and the mixture was refluxed 18 h. The cooled reaction mixture was diluted with 150 mL THF and treated dropwise with 10 mL H2O and 10 mL 5 N NaOH, respectively. The resulting gray mixture was refluxed 18 h, filtered and evaporated. The residue partially dissolved in hexane to give 25.5 g of crude yellow liquid and 6.9 g hexane insoluble starting carboxamide. HPLC purification on silica gel of the 25.5 g liquid, eluting with 20% MeOH-EtOAc gave 1-isopropylpiperidine-4-methylamine (8.5 g, 28%).

1. temperaturethe mixture was refluxed 18 h
2. customThe cooled reaction mixture
3. temperatureThe resulting gray mixture was refluxed 18 h
4. filtrationfiltered
5. customevaporated
6. dissolutionThe residue partially dissolved in hexane
7. customto give 25.5 g of crude yellow liquid and 6.9 g hexane insoluble
8. customHPLC purification on silica gel of the 25.5 g liquid
9. washeluting with 20% MeOH-EtOAc

ORD record

ord-ebc2cf3b7a07425bb25dbc4a1f417bb9

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06780878B2