Trifluoroacetic acid → HCID 68288631, compound

HRID 541292Notes

Reaction equation

HRID 541292 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH:11]([CH3:22])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[CH3:22][CH:11]1[CH2:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:14][CH2:13][NH:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68288745HCID 68288745, compound2×

Product 1

HCID 68288631HCID 68288631, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(4-cyanophenyl)-2-methylpiperidine-1-carboxylate (compound 176.2, 500 mg, 1.50 mmol, 1.00 equiv, 90%) in dichloromethane (3 mL) was added TFA dropwise (1 mL). The resulting mixture was stirred for 1.5 h at room temperature, then diluted with 30 mL of dichloromethane. The resulting mixture was washed with sodium bicarbonate (aq., 1 M. Note: significant gas evolution). The aqueous phase was extracted with 2×50 mL of dichloromethane and the combined organic layers were dried (Na2SO4), and concentrated in vacuo. The residue was purified using silica gel column chromatography with methanol/dichloromethane (1:50-1:20) as eluent to yield 280 mg (93%) of 4-(2-methylpiperidin-4-yl)benzonitrile as a colorless oil.

Workup

  1. washThe resulting mixture was washed with sodium bicarbonate (aq., 1 M. Note: significant gas evolution)
  2. extractionThe aqueous phase was extracted with 2×50 mL of dichloromethane
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-2309383dd48b461e8c49d301707a1be7
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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