Trifluoroacetic acid → 3,3-Dimethylpiperidin-4-one

HRID 12250

Reaction equation

HRID 12250 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:15][C:10]1([CH3:16])[C:11](=[O:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 222788373,3-Dimethylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3,3-dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester thus prepared (450 mg, 1.97 mmol) was dissolved in methylene chloride (10 mL). Trifluoroacetic acid was added (305 uL) and the resulting solution stirred at room temperature 2 h. Additional trifluoroacetic acid was added (300 uL) and the reaction stirred at room temperature 3 days. The pale yellow solution was concentrated to afford an oily residue, which was triturated with ether. The solids were collected by suction filtration and dried in vacuo. 3,3-Dimethyl-piperidin-4-one was isolated and used as its trifluoroacetic acid salt (381 mg, 80%).

Workup

  1. stirringthe reaction stirred at room temperature 3 days
  2. concentrationThe pale yellow solution was concentrated
  3. customto afford an oily residue, which
  4. customwas triturated with ether
  5. filtrationThe solids were collected by suction filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-56dffb8badf046c4b6812a170c7583af
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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