Acetic Acid → 1-(tert-Butoxycarbonyl)piperidine-4-carboxamide

HRID 1896236Notes

Reaction equation

HRID 1896236 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.[C:10]([OH:13])(=[O:12])C>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[C:5]([CH:4]1[CH2:8][CH2:9][N:1]([C:10]([O:13][C:4]([CH3:8])([CH3:5])[CH3:3])=[O:12])[CH2:2][CH2:3]1)(=[O:6])[NH2:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 37724-Piperidinecarboxamide

Product 1

HCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideYield 82.4%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of isonipecotamide (500 mg, 3.90 mmol) in a mixture of 5% aqueous sodium carbonate (7 ml) and 1,4-dioxane (3 ml) was added Boc-anhydride (1.30 ml, 5.85 mmol) and stirred for 5 h at room temperature. The pH was adjusted to 5-6 with acetic acid and volatiles were evaporated under vacuo. The residue was triturated with n-pentane and diethyl ether to yield 740 mg (82.4%) of tert-butyl 4-carbamoylpiperidine-1-carboxylate as a white solid.

Workup

  1. customwere evaporated under vacuo
  2. customThe residue was triturated with n-pentane and diethyl ether

Sources & evidence

ORD record
ord-d68ab69222b1449b84d32f80bec83237
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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