Trifluoroacetic acid → HCID 67208648, compound

HRID 711283Notes

Reaction equation

HRID 711283 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1)=[O:6].C(O)(C(F)(F)F)=O>ClCCl>[NH2:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:7]([C:5]([C:4]2[CH:22]=[CH:23][N:24]=[C:2]([F:1])[CH:3]=2)=[O:6])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67208646HCID 67208646, compound

Product 1

HCID 67208648HCID 67208648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-(2-fluoroisonicotinoyl)piperidin-4-yl)methylcarbamate 93-3 (1.81 g, 5.0 mmol) in dichloromethane (10 mL) was added TFA (5 mL) dropwise at room temperature. The mixture was stirred for 10 hours, and then the solvents were removed by rotary evaporation. The residue was dissolved in ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 solution, H2O and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation to give (4-(aminomethyl)piperidin-1-yl)(2-fluoropyridin-4-yl)methanone 93-4 as a yellow oil. MS m/z 238.1 (M+1)

Workup

  1. customthe solvents were removed by rotary evaporation
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3 solution, H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-9a8435679f2d4e0a9c93e9bbc1de6afa
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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