4-Piperidinecarboxamide → 1-(tert-Butoxycarbonyl)piperidine-4-carboxamide

HRID 1497643Notes

Reaction equation

HRID 1497643 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.[C:10]([O:14][C:15](OC([O-])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(#N)C.CN(C1C=CN=CC=1)C>[C:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:2][CH2:3]1)(=[O:8])[NH2:9]

Participants

5

Reactant 2

HCID 37724-PiperidinecarboxamideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideYield 74.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of piperidine-4-carboxamide (2 g, 15.6 mmol) in acetonitrile (30 mL), tert-butyldicarbonate (4.4 g, 20.2 mmol, 1.3 eq) and DMAP (190 mg, 1.56 mmol, 0.1 eq) were added and the mixture was stirred at r.t. overnight. It was then concentrated under reduced pressure, taken up with DCM and washed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, brine and water. The organic phase was dried over Na2SO4 and evaporated to dryness. The residue was triturated with diethyl ether and the white solid was filtered and dried to give 2.65 g (74%) of the title product.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. washwashed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, brine and water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was triturated with diethyl ether
  6. filtrationthe white solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-f3bc8bb2e890464f8e24be62d79ebc92
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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