Trifluoroacetic acid → 1-(Pyrimidin-2-yl)piperidin-4-amine

HRID 1485577Notes

Reaction equation

HRID 1485577 reaction equation
C(O)(C(F)(F)F)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[N:14]1[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1>C(Cl)Cl>[N:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[N:14]1[CH2:15][CH2:16][CH:17]([NH2:20])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 37967249HCID 37967249, compound

Product 1

HCID 47782331-(Pyrimidin-2-yl)piperidin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (7.87 mL, 103 mmol) was added to a solution of tert-butyl 1-(pyrimidine-2-yl)piperidin-4-ylcarbamate (2.86 g, 10.3 mmol) in DCM (60 mL) at at 0° C. The reaction mixture was stirred for 2 h at room temperature and removed the solvent under reduced pressure. The residue was re-dissolved in DCM, and neutralized with aq. Na2HCO3. The solvents were removed by evaporation, the resulting residue was purified by column chromatography (DCM:MeOH:NH4OH=10:1:0.1) to give 1-(pyrimidin-2-yl)piperidin-4-amine (1.68 g, 92%) as a white solid. 1H-NMR (CD3OD, Varian 400 MHz) δ 1.26-1.37 (2H, m), 1.75-1.99 (2H, m), 2.76-2.98 (2H, m), 2.86-3.05 (1H, m), 4.64-4.72 (2H, m), 6.53 (1H, t, J=4.8 Hz), 8.27 (2H, d, J=4.8 Hz). m/z=179.04 [M+1]+.

Workup

  1. customremoved the solvent under reduced pressure
  2. dissolutionThe residue was re-dissolved in DCM
  3. customThe solvents were removed by evaporation
  4. customthe resulting residue was purified by column chromatography (DCM:MeOH:NH4OH=10:1:0.1)

Sources & evidence

ORD record
ord-91fe8635e0c642f7afd934b67406b89d
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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