Hydrochloric Acid → 3-Phenylpiperidine

HRID 1781170Notes

Reaction equation

HRID 1781170 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O=[Pt]=O.O>[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 138863-Phenylpyridine

Product 1

HCID 1072073-PhenylpiperidineYield 90.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-phenylpyridine (8.0 g, 51.5 mmol), PtO2 (0.8 g), 234 mL of H2O, and 16 mL of concentrated HCl was hydrogenated in a Parr shaker at room temperature for 24 hours. The mixture was filtered, and the filtrate was cooled to 0° C. and was basified with 10N NaOH solution. The mixture was extracted (4×) with CH2Cl2. The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (7.5 g ) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.62 (t, 2H), 1.80 (m, 1H), 2.01 (m, 1H), 2.67 (m, 3H), 3.05-3.23 (m, 2H), 7.20 (d, 2H), 7.29 (t, 3H). MS (DCl/NH3) m/e 162 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. extractionThe mixture was extracted (4×) with CH2Cl2
  3. washThe combined organic layers were washed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-feaac4267df546c792d0547b62a1969a
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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