Methanol → Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate

HRID 1507501

Reaction equation

HRID 1507501 reaction equation
O[NH:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].CO>[Ni].C(O)(=O)C>[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=[NH:2])[NH2:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 178451986HCID 178451986, compound

Product 1

HCID 44828660Tert-butyl 4-carbamimidoylpiperidine-1-carboxylateYield 96.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Into a 2-L round-bottom flask purged and maintained with an inert atmosphere of argon, was placed tert-butyl 4-(N-hydroxycarbamimidoyl)piperidine-1-carboxylate (46.5 g, 181.56 mmol, 1.00 equiv, 95%), methanol (1500 mL), acetic acid (20 mL), and Raney-Ni (13 g). The reaction system was bubbled for 5 times with hydrogen. The resulting mixture was stirred for 3 h at 50° C. in an oil bath. The solids were filtered out. The resulting solution was concentrated under vacuum to afford 40 g of tert-butyl 4-carbamimidoylpiperidine-1-carboxylate as yellow green crude oil, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 278.

Workup

  1. customInto a 2-L round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of argon
  3. customThe reaction system was bubbled for 5 times with hydrogen
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-07e5935378e142639bd1e691f0f835f7
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Linked notes

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