Triethylamine → HCID 72309468, compound

HRID 2400541Notes

Reaction equation

HRID 2400541 reaction equation
[CH3:1][O:2][C:3]1([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.Cl.[NH2:18][OH:19].C(N(CC)CC)C>C(O)C.O>[OH:19][N:18]=[C:13]([C:12]1[CH:11]=[CH:10][C:9]([C:3]2([O:2][CH3:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[CH:16][CH:15]=1)[NH2:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59504696HCID 59504696, compound

Product 1

HCID 72309468HCID 72309468, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(4-methoxytetrahydro-2H-pyran-4-yl)benzonitrile (Step 1, 200 mg, 0.921 mmol), hydroxylamine hydrochloride (141 mg, 2.03 mmol) and triethylamine (205 mg, 2.03 mmol) in ethanol (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 (229 mg, 99%): 1H NMR (400 MHz, DMSO-d6) δ 9.63 (s, 1H), 7.68 (d, 2H), 7.39 (d, 2H), 5.80 (s, 2H), 3.71-3.67 (m, 4H), 2.88 (m, 2H), 1.93-1.89 (m, 4H); DCI(NH3)-MS m/z 251 (MH)+; HPLC RT (Method G) 2.95 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-95c755078338416dacfb462b76376d3f
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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