Trifluoroacetic acid → 4-Methyl-1-(piperidin-4-ylmethyl)piperazin-2-one

HRID 524909Notes

Reaction equation

HRID 524909 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[C:11](=[O:29])[CH2:10]1>C(Cl)Cl>[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:11](=[O:29])[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86720963Tert-butyl 4-((4-methyl-2-oxopiperazin-1-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 840358834-Methyl-1-(piperidin-4-ylmethyl)piperazin-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL, 12.98 mmol) was added to a stirred solution of tert-butyl 4-[(4-methyl-2-oxo-piperazin-1-yl)methyl]piperidine-1-carboxylate (98 mg, 0.3147 mmol) in DCM (2 mL) and the reaction stirred at ambient temperature for 16 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The residue was passed through a 5 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M NH3 in MeOH/DCM mixtures. The solvent was removed in vacuo to give 4-methyl-1-(piperidin-4-ylmethyl)piperazin-2-one as a colourless oil (65 mg, 98% Yield). MS (ES+) 212.0.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. washwashed with MeOH/DCM
  4. washThe product was eluted
  5. washby washing the cartridge with 2M NH3 in MeOH/DCM mixtures
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-488a77ec1e5e452d8338397986028df0
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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