Triethylamine → 4-(4-Fluorotetrahydro-2H-pyran-4-yl)-N'-hydroxybenzenecarboximidamide

HRID 2400539Notes

Reaction equation

HRID 2400539 reaction equation
[F:1][C:2]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C.O>[F:1][C:2]1([C:8]2[CH:15]=[CH:14][C:11]([C:12](=[N:17][OH:18])[NH2:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 595046564-(4-Fluorotetrahydro-2H-pyran-4-yl)benzonitrile

Product 1

HCID 723094834-(4-Fluorotetrahydro-2H-pyran-4-yl)-N'-hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(4-fluorotetrahydro-2H-pyran-4-yl)benzonitrile (Step 1, 180 mg, 0.877 mmol), hydroxylamine hydrochloride (134 mg, 1.93 mmol) and triethylamine (196 mg, 1.93 mmol) in ethanol (4.5 mL) was stirred and heated at reflux for 4 h. After being cooled to rt, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate. The organic extract was successively washed with brine and dried over anhydrous magnesium sulfate. After filtration and evaporation of the solvent, the title compound was obtained (201 mg, 76%): 1H NMR (500 MHz, DMSO-d6) δ 9.64 (s, 1H), 7.70 (d, 2H), 7.44 (d, 2H), 5.81 (s, 2H), 3.88-3.83 (m, 2H), 3.73-3.67 (m, 2H), 2.23-2.06 (m, 2H), 1.87-1.81 (m, 2H); DCI(NH3)-MS m/z 239 (MH)+; HPLC RT (Method I) 3.13 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas successively washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-8bec18c962cb43f4af62530cb6d18005
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

Loading…