Trifluoroacetic acid → 1-(2-Methoxyethyl)piperidin-4-amine

HRID 2241406Notes

Reaction equation

HRID 2241406 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7][CH2:6]1.FC(F)(F)C(O)=O>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([NH2:11])[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53256198tert-Butyl 1-(2-methoxyethyl)piperidin-4-ylcarbamate

Product 1

HCID 201191211-(2-Methoxyethyl)piperidin-4-amineYield 37.8%

Procedure

A mixture of tert-butyl 1-(2-methoxyethyl)piperidin-4-ylcarbamate (0.842 g, 3.26 mmol) and 2,2,2-trifluoroacetic acid (2.51 ml, 32.6 mmol) was stirred for 15 minutes at ambient temperature. The mixture was concentrated in vacuo, using toluene (2×10 mL) to azeotrope residual TFA. The crude TFA salt of the product was converted to the free base using Biotage Flash 40M flash chromatography, eluting with 10% MeOH (containing 7N NH3) in DCM (500 mL), followed by 20% MeOH (containing 7N NH3) in DCM (500 mL). The product was obtained as an oil (195 mg, 37%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washeluting with 10% MeOH (containing 7N NH3) in DCM (500 mL)

Sources & evidence

ORD record
ord-49b8a5f97d11434bb49b5f392ef55077
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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