Tert-Butylamine → 1-tert-Butyl-4-piperidone

HRID 2109271Notes

Reaction equation

HRID 2109271 reaction equation
[I-].C[N+]1(C)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>O.CO>[C:11]([N:15]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 111494971,1-Dimethyl-4-oxopiperidin-1-ium iodide

Product 1

HCID 738401-tert-Butyl-4-piperidoneYield 4.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 64.5 g (253 mmol) of 1,1-dimethyl-4-oxo-piperidinium iodide in 50 mL of water and 90 mL (860 mmol) of tert-butylamine was stirred for 15 min when 1.0 mL of 40% Triton B in MeOH was added. The mixture was refluxed for 2 hr under N2, and then it was extracted with Et2O (4×100 mL). The aqueous phase was basified with 20 g of NaOH in 20 mL of water, and then it was extracted further with Et2O (4×100 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated. The residual oil was shaken with 1.5 L of petroleum ether, which was decanted and concentrated. The residue was distilled under vacuum to provide 1.8 g of 1-tert-butyl-piperid-4-one.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 2 hr under N2
  3. extractionit was extracted with Et2O (4×100 mL)
  4. extractionit was extracted further with Et2O (4×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customwas decanted
  10. concentrationconcentrated
  11. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-1852706a9d0547b596d1c6e36b0d104b
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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