Trifluoroacetic acid → 2-(4-Aminopiperidin-1-yl)ethan-1-ol

The 4-(N-Boc amino)-1-piperidineethanol (13 g, 53.2 mmol) was treated with TFA (26 mL) for 90 mL. The TFA was removed (reduced pressure) and the TEA salt was converted to the HCl salt by treatment with 20% HCl/methanol (130 mL) at ambient temperature for 30 min. The HCl/methanol was evaporated (reduced pressure) and the residue dissolved in H2O (10 mL). The solution was cooled in an ice-bath and NaOH (10M, 35 mL) added to pH >10. The solution was warmed to RT and stirred for 15 min prior to evaporating to dryness. The residue was triturated with ether/isopropanol (2:1), filtered and evaporated to dryness. The trituration process was repeated until no salt was present in the oil (5×) to yield 6.7 g (87%) of an off-white solid.

1. customThe TFA was removed (reduced pressure)
2. customThe HCl/methanol was evaporated (reduced pressure)
3. dissolutionthe residue dissolved in H2O (10 mL)
4. temperatureThe solution was cooled in an ice-bath
5. additionNaOH (10M, 35 mL) added to pH >10
6. customto evaporating to dryness
7. customThe residue was triturated with ether/isopropanol (2:1)
8. filtrationfiltered
9. customevaporated to dryness

ORD record

ord-72f17d7219ce40aaa5527fca5882ba95

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409122B2