Triethylamine → HCID 61286981, compound

HRID 2400560Notes

Reaction equation

HRID 2400560 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.Cl.[NH2:18][OH:19].C(N(CC)CC)C>C(O)C>[OH:19][N:18]=[C:13]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:16][CH:15]=1)[NH2:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 55139138HCID 55139138, compound

Product 1

HCID 61286981HCID 61286981, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[(tetrahydro-2H-pyran-4-yloxy)methyl]benzonitrile (Step 1, 780 mg, 3.59 mmol), hydroxylamine hydrochloride (549 mg, 7.90 mmol) and triethylamine (1.10 mL, 7.90 mmol) in ethanol (20 mL) was stirred and heated at reflux for 1 h. After being cooled to rt, the reaction mixture was evaporated to dryness. The resulting material was treated with ethyl acetate, and the solid was filtered off. The ethyl acetate solution was washed with water and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was stirred in hexane and filtered. After evaporation of the solvent, the title compound was obtained (857 mg, 95%): 1H NMR (400 MHz, CDCl3) δ 7.55 (d, 2H), 7.40 (d, 2H), 4.81 (s, 2H), 4.06-3.99 (dd, 2H), 3.81 (d, 2H), 3.48-3.40 (m, 2H), 2.15-2.02 (m, 1H), 1.78-1.72 (dd, 2H), 1.52-1.40 (m, 2H); ES-MS m/z 251, HPLC RT (Method E) 0.56 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe reaction mixture was evaporated to dryness
  4. additionThe resulting material was treated with ethyl acetate
  5. filtrationthe solid was filtered off
  6. washThe ethyl acetate solution was washed with water and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customAfter evaporation of the solvent
  10. filtrationfiltered
  11. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-fff92d16b396442e98a2a403fbcc33bb
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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