HCID 12248299, compound → 4-tert-butylpiperidine Hydrochloride

HRID 1518953Notes

Reaction equation

HRID 1518953 reaction equation
[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]>[Pt](=O)=O.CCO>[ClH:1].[C:2]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 12248299HCID 12248299, compound

Product 1

HCID 27946764-tert-butylpiperidine HydrochlorideYield 92%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

Place 4-tert-butylpyridine hydrochloride (50 g, 277 mmol) in a PARR reactor and add EtOH (350 mL) followed by platinum (IV) oxide (5.0 g, 22.02 mmol). Stir the mixture at 22° C. under a hydrogen atmosphere (500 psi) for 18 hours. Evacuate the excess hydrogen and filter the suspension the a Celite® pad. Concentrate the filtrate and dry the residue under vacuum (40° C., 5 mbar) to give the title compound as an off-white solid (45.1 g, 92%). 1H-NMR (d6-DMSO) δ 0.83 (s, 9H), δ 1.2-1.5 (m, 3H), δ 1.7 (d, 2H), δ 2.7-2.8 (m, 2H), δ 3.2 (d, 2H), δ 8.7-9.3 (2 bs, 2H).

Workup

  1. customEvacuate the excess hydrogen
  2. filtrationfilter the suspension the a Celite® pad
  3. concentrationConcentrate the filtrate
  4. customdry the residue under vacuum (40° C., 5 mbar)

Sources & evidence

ORD record
ord-f7158485e9c54916bde975dc196c47f0
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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