trans-{3-Azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine → trans-{3-Aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

HRID 896556Notes

Reaction equation

HRID 896556 reaction equation
[N:1]([CH2:4][C@H:5]1[C@H:10]([N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH2:9][CH2:8][N:7]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:6]1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][C@H:5]1[C@H:10]([N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH2:9][CH2:8][N:7]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 86591725trans-{3-Azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

Product 1

HCID 69736700trans-{3-Aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of crude trans-{3-azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine (106 mg, 278 μmol) and 10% palladium on charcoal (20 mg) in ethanol (5 mL) was stirred at room temperature under a hydrogen atmosphere. After 1.75 hours, the mixture was filtered through Celite and the solids were rinsed with ethanol. The filtrate was concentrated to provide a gum (98 mg, quantitative). 1H NMR (300 MHz, CDCl3) δ7.33 (m, 5H), 7.15 (m, 2H), 6.98 (t, J=9 Hz, 2H), 3.72 (d, J=13 Hz, 1H), 3.55 (d, J=13 Hz, 1H), 3.07 (m, 2H), 2.9-2.7 (m, 4H), 2.55 (m, 2H), 2.37 (m, 1H), 2.23 (s, 3H), 2.19 (m, 2H), 2.0-1.6 (m, 5H). Mass spec (AP+) m/z 356.2 (M+H+).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washthe solids were rinsed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customto provide a gum (98 mg, quantitative)

Sources & evidence

ORD record
ord-c2f02f419b03483aa9ba46ab6637b6f4
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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