Acetic Acid → Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate

HRID 419706

Reaction equation

HRID 419706 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:17])[NH:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[H][H]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:15])[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178451986HCID 178451986, compound

Product 1

HCID 44828660Tert-butyl 4-carbamimidoylpiperidine-1-carboxylateYield 114.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Dissolve 4-(N-Hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (9.7 g 1.00 equiv; 39.9 mmoles) in methanol (300 mL) and add acetic acid (2 equiv, 79.73 mmoles; 4.6 mL), and methanol washed Raney Nickel (2.7 g). Heat the reaction to 50° C., then hydrogenate with 1 ATM hydrogen gas for 4.5 hours. Filter the reaction mixture through Celite and concentrate under reduced pressure. Suspend the solid in diethyl ether, filter and dry under reduced pressure to give 10.39 g of 4-carbamimidoyl-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. washwashed Raney Nickel (2.7 g)
  2. temperatureHeat
  3. customthe reaction to 50° C.
  4. filtrationFilter the reaction mixture through Celite
  5. concentrationconcentrate under reduced pressure
  6. filtrationfilter
  7. customdry under reduced pressure

Sources & evidence

ORD record
ord-e6789619158c43e48ac3e8cf85a31415
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Linked notes

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