Trifluoroacetic acid → Methyl 3-(3-aminopiperidin-1-yl)benzoate

HRID 602161Notes

Reaction equation

HRID 602161 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]2[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=2)[C:25]([O:27][CH3:28])=[O:26])[CH2:17]1)=O)(C)(C)C>ClCCl>[NH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]2[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=2)[C:25]([O:27][CH3:28])=[O:26])[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58992690Methyl 3-[3-(tert-butoxycarbonylamino)piperidin-1-yl]benzoate

Product 1

HCID 58992611Methyl 3-(3-aminopiperidin-1-yl)benzoateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to methyl 3-[3-(tert-butoxycarbonylamino)piperidin-1-yl]benzoate (451 mg, 1.35 mmol) in dichloromethane (2 mL). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the mixture was concentrated and a saturated aqueous sodium bicarbonate solution was added to the residue to make it basic. The mixture was extracted with ethyl acetate and the organic layer washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave 158 mg (50%) of the desired compound as a pale yellow oil.

Workup

  1. concentrationSubsequently, the mixture was concentrated
  2. additiona saturated aqueous sodium bicarbonate solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9e2848ca960545a1bf7b7cc77d96c5f3
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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