Butyl bromide → (1-Butylpiperidin-4-yl)methanol

A mixture of ethyl isonipecotate (102 g, 0.65 mole) and 1-bromobutane (72 ml, 0.67 mole) in ethanol (1.2 L) was treated with anhydrous potassium carbonate (180 g, 1.3 mole) and heated under reflux for 2 h. The mixture was allowed to cool an then filtered through kieselguhr. The filtrate was concentrated in vacuo to leave a yellow oil, which was dissolved in ether (300 ml) and added dropwise over 20 minutes to a stirred suspension of lithium aluminium hydride (50 g, 1.3 mole) in ether (500 ml) at 0° C. under nitrogen. The mixture was stirred at room temperature for 18 h, then cooled to 0° C. and treated with water (50 ml), 10% NaOH solution (50 ml) and water (150 ml). The mixture was filtered through keiselguhr and the filtrate concentrated under vacuum to leave a pale yellow oil, which was distilled to afford the title compound as a colourless oil (88.5 g, 80%) bp 102°-108° C. at 0.1 mm Hg.

1. temperatureheated
2. temperatureunder reflux for 2 h
3. temperatureto cool
4. filtrationan then filtered through kieselguhr
5. concentrationThe filtrate was concentrated in vacuo
6. customto leave a yellow oil, which
7. temperaturecooled to 0° C.
8. filtrationThe mixture was filtered through keiselguhr
9. concentrationthe filtrate concentrated under vacuum
10. customto leave a pale yellow oil, which
11. distillationwas distilled

ORD record

ord-bd69793581e549369665e00920da4831

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05696129