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

HRID 552254Notes

Reaction equation

HRID 552254 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%). 1H-NMR (d6-DMSO, 300 MHz) δ 3.44-3.33 (m, 4H), 2.63-2.57 (m, 2H), 1.11 (s, 6H).

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-c496d36e98df4d28a94d59a146beae36
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

Loading…