(2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt → 6-Ethyl-2-phenyl-piperidin-3-ylamine

To a 250 ml Parr bottle was charged 1 gm (3.18 mmol) of the (2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt prepared above in 60 ml of methanol. To the resulting solutionwas added an excess of commercial Raney nickel which had been exhaustively washed with deionized water until the supernatant was pH 7.00. The reaction mixture was placed under 50 p.s.i. in a Parr Hydrogenator and shaken for 4 hrs. The reaction mixture was filtered through celite and the filtrate was evaporated in vacuo. The residue was partitioned between methylene chloride and 1N NaOH. The combined organics were washed with brine and then dried and evaporated to afford 0.47 gm (72%) of crude racemic 6-Ethyl-2-phenyl-piperidin-3-ylamine. Such racemate was resolved through the formation of a salt with (−)-O,O′-dibenzoyl-L-tartaric acid in isopropanol water. 1H NMR (CDCl3, 400 MHz) δ 7.4–7.2 (br.m, 5H), 4.05 (d), 3.0 (br.t), 2.90 (m), 1.98 (m), 1.75 (m), 1.6–1.4 (m), 0.80 (t, 3H), ppm. Mass spectra m/z=205 (p+1).

1. washhad been exhaustively washed with deionized water until the supernatant
2. filtrationThe reaction mixture was filtered through celite
3. customthe filtrate was evaporated in vacuo
4. customThe residue was partitioned between methylene chloride and 1N NaOH
5. washThe combined organics were washed with brine
6. customdried
7. customevaporated

ORD record

ord-fa35ce59ff0a4842b32be574a710c37c

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119207B2