Methyl 2-(4-tert-butylphenyl)isonicotinate hydrochloride → Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride

HRID 1963154Notes

Reaction equation

HRID 1963154 reaction equation
[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]>CO.[Pt](=O)=O>[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][CH2:20][NH:21]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66731754Methyl 2-(4-tert-butylphenyl)isonicotinate hydrochloride

Product 1

HCID 66731791Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-tert-butylphenyl)isonicotinate hydrochloride (9.6 g, 31.39 mmol) in MeOH (100 mL) was added platinum(IV) oxide (0.713 g, 3.14 mmol). The resulting mixture was hydrogenated in a Büchi hydrogenator at 5 bar. After 8 h the reaction mixture was filtered through a diatomeous earth filter carton, the residue washed with methanol, and the filtrate evaporated. Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride (9.66 g, 99%) was isolated as a brown solid. 1H NMR (400 MHz, dmso) δ 1.26 (s, 9H), 1.88-2.15 (m, 4H), 2.82-2.92 (m, 1H), 3.03-3.16 (m, 1H), 3.27-3.38 (m, 1H), 3.61 (s, 3H), 4.22-4.29 (m, 1H), 7.42-7.53 (m, 4H), 9.43 (br, 2H). MS m/z 276 (M+H)+

Workup

  1. filtrationAfter 8 h the reaction mixture was filtered through a diatomeous earth
  2. filtrationfilter carton
  3. washthe residue washed with methanol
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-fea90a1da0534cc8b975a6ba6dadb9b5
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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