Benzene, 1-iodo-4-(trifluoromethyl)- → HCID 68731553, compound

HRID 2382192Notes

Reaction equation

HRID 2382192 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Li]CCCC.[C:17]([CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[OH:24][C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)[CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 10827307Tert-butyl 4-benzoylpiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 68731553HCID 68731553, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-iodo-4-(trifluoromethyl)benzene (0.92 g, 3.4 mmol) in dry THF at −78° C. was added n-BuLi (3 mL, 1.6 M in hexane) dropwise and the mixture was stirred at the same temperature for 30 min. To this was added a solution of tert-butyl 4-benzoylpiperidine-1-carboxylate (1.0 g, 3.4 mmol) in minimum amount of dry THF dropwise and the resulting reaction mixture was allowed to warm up to rt over 2 h. The reaction was quenched with ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to afford tert-butyl 4-(hydroxy(phenyl)(4-(trifluoromethyl)phenyl)methyl)-piperidine-1-carboxylate (1.0 g, 66% yield) as a pale yellow solid which was used in the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97d1c97e4a6742aabda23270c82860ad
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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