trans-3-Azidomethyl-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidine → trans-1-[2-(4-Fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine

HRID 896540Notes

Reaction equation

HRID 896540 reaction equation
[N:1]([CH2:4][C@H:5]1[C@H:10]([CH3:11])[CH2:9][CH2:8][N:7]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:6]1)=[N+]=[N-]>[Pd].C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][N:7]2[CH2:8][CH2:9][C@@H:10]([CH3:11])[C@H:5]([CH2:4][NH2:1])[CH2:6]2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 86591721trans-3-Azidomethyl-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidine

Product 1

HCID 69738210trans-1-[2-(4-Fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of trans-3-azidomethyl-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidine (252 mg, 911 μmol) and 10% palladium on charcoal (90 mg) in ethanol (25 mL) was shaken under a hydrogen atmosphere (60 psig) for 4 hours. The mixture was filtered and the filtrate was concentrated under vacuum to provide a sticky solid (226 mg, quantitative). 1H NMR (300 MHz, CDCl3) δ7.16 (m, 2H), 6.97 (t, J=9 Hz, 2H), 3.12 (m, 1H), 2.98 (m, 1H), 2.93 (dd, J=13, 3 Hz, 1H), 2.80 (m, 2H), 2.58 (m, 3H), 1.99 (m, 1H), 1.80 (m, 1H), 1.8-1.6 (m, 3H), 1.5-1.1 (m, 3H), 0.97 (d, J=6 Hz, 3H). Mass spec (ES+) m/z 251.1 (M+H+, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto provide a sticky solid (226 mg, quantitative)

Sources & evidence

ORD record
ord-53921c4d3a4b4260ba9b766dcff558c2
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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