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

HRID 1043797Notes

Reaction equation

HRID 1043797 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, 0.5676 mmol, 1 eq) in dichloromethane, stirring at room temperature for 1 hour. The solvent was then evaporated, the residue 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-bbfe9f3624384ce1a3e83c2488aad6de
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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