Hydrochloric Acid → 4-[(Piperidin-4-yl)methyl]aniline

HRID 634832

Reaction equation

HRID 634832 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O>C(O)C.[Pt](=O)=O>[NH:12]1[CH2:13][CH2:14][CH:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 141294-(4-Nitrobenzyl)pyridine

Product 1

HCID 109978244-[(Piperidin-4-yl)methyl]anilineYield 86.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110-113° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with cold water and basified with 10% sodium hydroxide solution
  3. extractionThe resulting mixture was extracted into ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue on crystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1c56253fd1cd4e318801626525f419b7
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Linked notes

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