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

HRID 515273Notes

Reaction equation

HRID 515273 reaction equation
[Br:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18542613Tert-butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 623476394-(2-Bromo-4-nitrophenoxy)piperidineYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylate (12.21 mmol, 4.9 g) was dissolved in dichloromethane (40 mL) and trifluoroacetic acid (73.3 mmol, 8.35 g) added. The mixture was stirred at room temperature for 3 hours before concentrating under reduced pressure. The resulting residue was dissolved in dichloromethane (150 mL) and washed with a saturated solution of sodium bicarbonate (3×50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound (3.3 g).

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dichloromethane (150 mL)
  3. washwashed with a saturated solution of sodium bicarbonate (3×50 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-157047b09cd64502ad69424ba9779bf6
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…