Sodium Bicarbonate → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 1781171Notes

Reaction equation

HRID 1781171 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].[C:15](OC([O-])=O)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(OCC)(=O)C>[C:18]([O:17][C:15]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723901PiperonylamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Piperidone monohydrate hydrochloride (5 g, 0.033 mol) was added to 50 mL distilled water and stirred until dissolved. To this solution was added solid sodium bicarbonate (3 g, 0.035 mol) followed by tert-butyl dicarbonate (7.2 g, 0.033 mol), and the resulting clear solution was stirred for 20 hours at room temperature. The slurry was treated with 100 mL of ethyl acetate and stirred until all solids dissolved. The layers were separated, and the organic layer was washed with 30 mL of 1N H3PO4 and 30 mL of 10% NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 5.6 g (86%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 3.75-3.68 (t, 4H), 2.47-2.40 (t, 4H), 1.5 (s, 9H). MS (DCl/NH3) m/e 200 (M+H)+, 217 (M+H+NH3)+.

Workup

  1. distillationdistilled water
  2. dissolutionuntil dissolved
  3. stirringthe resulting clear solution was stirred for 20 hours at room temperature
  4. stirringstirred until all solids
  5. dissolutiondissolved
  6. customThe layers were separated
  7. washthe organic layer was washed with 30 mL of 1N H3PO4 and 30 mL of 10% NaCl
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9cb6e4061fd47429f9ca4cb6f7de7c1
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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