Triethylamine → N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)trifluoroacetamide

HRID 1978342Notes

Reaction equation

HRID 1978342 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[F:23][C:24]([F:31])([F:30])[C:25](OCC)=[O:26]>C(#N)C>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:25](=[O:26])[C:24]([F:31])([F:30])[F:23])[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 21994020N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)trifluoroacetamideYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.07 g (23.7 mM) of tert-butyl 4-aminomethylpiperidine-1-carboxylate and 5.0 ml (35.9 mM) of triethylamine in acetonitrile (40 ml) was added 5.6 ml (47.1 mM) of ethyl trifluoroacetate at room temperature and the mixture was stirred at room temperature for 1.5 hours. After the solvent was distilled off under reduced pressure, the residue was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. The solvent was then distilled off under reduced pressure to provide the title compound as light-yellow solid (6.40 g, 87%).

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and saturated aqueous solution of sodium chloride
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-2b40047e704b46ddb68aba63759d5e5d
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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