Ammonium Acetate → HCID 178506376, compound

HRID 419705Notes

Reaction equation

HRID 419705 reaction equation
O=[C:2]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=O.C([O-])(=O)C.[NH4+:35]>C(O)(=O)C>[F:28][C:27]([F:30])([F:29])[O:26][C:22]1[CH:21]=[C:20]([C:2]2[N:35]=[C:5]([CH:7]3[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]3)[NH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 66650102Tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 178506376HCID 178506376, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)-piperidine-1-carboxylate (1.50 g, 3.48 mmol) to a mixture of ammonium acetate (1.40 g, 18.1 mmol), and glacial acetic acid (10 mL) and heat at reflux for 15 h. Cool the mixture to room temperature and concentrated in vacuo. Dissolve the residue in ethyl acetate (50 mL) and adjust to pH 8 with saturated NaHCO3. Extract the aqueous layer with ethyl acetate (2×50 mL). Combine the organic layers, dry (Na2SO4), filter, and concentrate in vacuo. Purify the residue by silica gel chromatography (80 g, eluting with a gradient of 10% to 20% methanol/ethyl acetate, 1.5 L) to provide 4-(4-(3-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)piperidine (491 mg, 45%).

Workup

  1. temperatureheat
  2. temperatureat reflux for 15 h
  3. concentrationconcentrated in vacuo
  4. dissolutionDissolve the residue in ethyl acetate (50 mL)
  5. extractionExtract the aqueous layer with ethyl acetate (2×50 mL)
  6. dry with materialCombine the organic layers, dry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the residue by silica gel chromatography (80 g
  10. washeluting with a gradient of 10% to 20% methanol/ethyl acetate, 1.5 L)

Sources & evidence

ORD record
ord-ec672467612543f5990e403f1f8aded9
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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