4-Piperidone hydrochloride → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 1871920Notes

Reaction equation

HRID 1871920 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:9](=O)([O:15]C(C)(C)C)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]>O1CCOCC1.O.C(N(CC)CC)C>[C:11]([O:10][C:9]([N:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]1)=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 30848514-Piperidone hydrochlorideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

4-Ketopiperidine hydrochloride (48.3 g) and di-tert-butyl carbonate (93.2 g) were dissolved in a dioxane-water equivolume mixture (1000 ml), and triethylamine (119 ml) was added to the resultant mixture. The mixture was stirred at room temperature for five hours and concentrated under reduced pressure. Water and ethyl acetate were added to the residue. After separation of the organic phase, the organic phase was washed with a saturated solution of potassium hydrogensulfate and water, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby obtain the title compound as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate were added to the residue
  3. customAfter separation of the organic phase
  4. washthe organic phase was washed with a saturated solution of potassium hydrogensulfate and water
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4e61fced110421d873f0cab193649c4
Source dataset
uspto-grants-2000_08
Patent number
US06107308

Reaction notes

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