Trifluoroacetic acid → 4-(Azetidine-1-carbonyl)piperidine

HRID 426084Notes

Reaction equation

HRID 426084 reaction equation
[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[O:6])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23658779tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate

Product 1

HCID 236587804-(Azetidine-1-carbonyl)piperidineYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(azetidin-1-ylcarbonyl)piperidine-1-carboxylate (0.50 g, 1.86 mmol) was dissolved in methylene chloride (10 mL) and to the solution was added trifluoroacetic acid (2.12 g, 18.6 mmol). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. The residue was dissolved in a small amount of methanol and THF and the solution was then loaded on a cation exchange sorbent (Isolute® SCX-2; 10 g). The column washed with THF and the product was then eluted with ammonia saturated methanol. The solvent was removed by evaporation. There was obtained 0.32 g (100%) of 4-(azetidin-1-ylcarbonyl)piperidine. 1H NMR (500 MHz, CDCl3): 1.4-1.5 (m, 4H), 2.0-2.2 (m, 3H), 2.4-2.5 (m, 2H), 2.9-3.0 (d, 2H), 3.7-3.8 (t, 2H), 3.9 (s, 1H), 4.0 (t, 2H).

Workup

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in a small amount of methanol and THF
  3. washThe column washed with THF
  4. washthe product was then eluted with ammonia saturated methanol
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-0a8d6dea2fee4d158928244235de5d67
Source dataset
uspto-grants-2012_01
Patent number
US08106208B2

Reaction notes

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