Trifluoroacetic acid → N-Benzyl-N-methyl-2-(piperidin-4-yl)ethanamine

HRID 1193336Notes

Reaction equation

HRID 1193336 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([N:15]([CH3:31])[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[CH2:8]([N:15]([CH3:31])[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19261850tert-Butyl 4-(2-(benzyl(methyl)amino)ethyl)piperidine-1-carboxylate

Product 1

HCID 19085399N-Benzyl-N-methyl-2-(piperidin-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.78 ml) was added dropwise at 0° C. to a solution of tert-butyl 4-(2-(benzyl(methyl)-amino)ethyl)piperidine-1-carboxylate (600 mg, 1.8 mmol, 1 eq) in dichloromethane (30 ml), and stirring was carried out for 1 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was concentrated to dryness. The residue was dissolved in MeOH (50 ml), Amberlyst A-21 ion-exchanger resin (2 g) was added, and stirring was carried out for 30 min. The reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure and used in the next stage without being purified further.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in MeOH (50 ml)
  3. additionAmberlyst A-21 ion-exchanger resin (2 g) was added
  4. stirringstirring
  5. waitwas carried out for 30 min
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated to dryness under reduced pressure
  8. customwithout being purified further

Sources & evidence

ORD record
ord-2e3ef4c773794b22ae3c39085d0739a8
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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