Methylamine → tert-Butyl 4-(methylamino)piperidine-1-carboxylate

HRID 225816Notes

Reaction equation

HRID 225816 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H][H].[CH3:17][NH2:18]>[Pd]>[CH3:17][NH:18][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10% Pd/C (2 g) was added to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (20 g, 100 mmol) in methylamine (33% in ethanol, 10 mL) and the mixture was stirred at room temperature, under 60 psi of hydrogen, for 18 hours. The reaction mixture was then filtered through Arbocel® and the filtrate was concentrated in vacuo. The residue was azeotroped with dichloromethane (×3) and the dried under vacuum for 72 hours to afford the title compound as a solid in 98% yield, 21.1 g. LRMS APCI m/z 215 [M+H]+

Workup

  1. filtrationThe reaction mixture was then filtered through Arbocel®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was azeotroped with dichloromethane (×3)
  4. customthe dried under vacuum for 72 hours

Sources & evidence

ORD record
ord-f335190cd70f469bad541b50d840da31
Source dataset
uspto-grants-2009_07
Patent number
US07557131B2

Reaction notes

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