Trifluoroacetic acid → 4-(2-Methoxy-4-nitrophenoxy)piperidine

HRID 1512122Notes

Reaction equation

HRID 1512122 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:11]=1[O:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1>ClCCl>[CH3:8][O:9][C:10]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:11]=1[O:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18542820HCID 18542820, compound

Product 1

HCID 550361544-(2-Methoxy-4-nitrophenoxy)piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 eq) was added to a solution of tert-butyl 4-(2-methoxy-4-nitrophenoxy)piperidine-1-carboxylate (200 mg, 0.57 mmol, 1 eq) in dichloromethane, stirring at room temperature for 1 hour. The solvent was then evaporated, the residue was brought to pH 10 with sat. aq. Na2CO3 solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and evaporated to afford the product 4-(2-methoxy-4-nitrophenoxy)piperidine as a light yellow solid (137.3 mg, 96%). LC/MS (m/z): 253.2 (MH+), Rt 1.81 minutes.

Workup

  1. customThe solvent was then evaporated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-45feda3b7d104df7b9be311e3d07d5b2
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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