Isobutylamine → tert-Butyl 4-(isobutylamino)piperidine-1-carboxylate

HRID 2111884Notes

Reaction equation

HRID 2111884 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17]>C(O)C.[Pd]>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 15380699tert-Butyl 4-(isobutylamino)piperidine-1-carboxylateYield 80.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 10% Pd/C (3.0 g, 10% wt), under nitrogen, is added a solution of the 1-Boc-4-piperidone (30 g, 150.6 mmol, 1.0 eq.) and isobutylamine (11.2 g, 180.3 mmol, 1.2 eq) in ethanol (300 ml). This is hydrogenated for 1.5 h at 65 psi using a Parr hydrogenator. The catalyst is removed by filtration through Celite. Solvent is removed under vacuum to give 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester as a colourless oil (31.2 g) with >98% purity. Mass spectrum (LCMS) Rt=2.79 (6 min gradient) (M++1) 257.2; 1H NMR (CDCl3): δ=4.01 (2H, brs), 2.82-2.75 (2H, m), 2.61-2.54 (1H, m), 2.43 (2H, d), 1.85-1.81 (2H, m), 1.76-1.67 (1H, m), 1.56 (1H, br s), 1.45 (9H, s), 1.31-1.18 (2H, m), 0.91 (6H, d).

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customSolvent is removed under vacuum

Sources & evidence

ORD record
ord-39304ba1c1f64294bd890b0b185a191d
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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