Methanol → 1-Boc-4-(aminomethyl)piperidine

HRID 659091Notes

Reaction equation

HRID 659091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:17][NH2:18]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:17][NH2:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 7368171-Boc-4-(aminomethyl)piperidineYield 93.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-tert-Butoxycarbonylpiperid-4-one (6.18 g, 31 mmol) was dissolved in a 2.0 M solution of methylamine in methanol (56 mL, 112 mmol). This solution was added to 10% palladium on carbon (wet, 1.3 g) and the mixture placed under an atmosphere of hydrogen for 72 h. The reaction mixture was then purged with nitrogen and filtered through a pad of Celite, which was then washed with methanol. The resulting hazy filtrate was filtered through a 0.2 μm filter and then concentrated in vacuo to afford the title intermediate (6.16 g, 29 mmol, 93.5% yield).

Workup

  1. customThe reaction mixture was then purged with nitrogen
  2. filtrationfiltered through a pad of Celite, which
  3. washwas then washed with methanol
  4. filtrationThe resulting hazy filtrate was filtered through a 0.2 μm
  5. filtrationfilter
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-970b30ed63854ca1aafa06de28c6e207
Source dataset
uspto-grants-2011_12
Patent number
US08080565B2

Reaction notes

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