Trifluoroacetic acid → 4-(3-(4-(2,2,2-Trifluoroethoxy)phenoxy)benzylidene)piperidine

HRID 1666527Notes

Reaction equation

HRID 1666527 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=2)[CH:13]=[C:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[F:33][C:2]([F:1])([F:32])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=2)[CH:13]=[C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876113HCID 66876113, compound

Product 1

HCID 668761824-(3-(4-(2,2,2-Trifluoroethoxy)phenoxy)benzylidene)piperidineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)benzylidene)piperidine-1-carboxylate (50 mg, 0.107 mmol) in dichloromethane (5 mL) was cooled to 0° C. and treated with trifluoroacetic acid (123 mg, 1.07 mmol) dropwise. The reaction mixture was then allowed to warm to room temperature and stirred at that temperature overnight. The reaction was concentrated, and the residue was dissolved in water (5 mL). The aqueous layer basified up to pH ˜8 with 1M sodium hydroxide solution. The aqueous layer was extracted with dichloromethane (3×20 mL), and organic layers were washed with water (2×10 mL), dried over sodium sulfate, and concentrated to give the crude title compound (40 mg, quant.)

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in water (5 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×20 mL), and organic layers
  4. washwere washed with water (2×10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d51a20da7d5c41dcb6e8cb63e1688cea
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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