Triethylamine → HCID 73853505, compound

HRID 590391Notes

Reaction equation

HRID 590391 reaction equation
Cl.[NH2:2][OH:3].CCN(CC)CC.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>CCO>[OH:3][N:2]=[C:23]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)=[CH:26][CH:25]=1)[NH2:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21927824HCID 21927824, compound2×

Product 1

HCID 73853505HCID 73853505, compoundYield 142.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (365 mg, 5.25 mmol) in EtOH (3 mL) was added Et3N (0.78 mL, 5.6 mmol) at room temperature under argon. A white precipitate formed. It was stirred at that temperature for 40 minutes. Then 4-[(tetrahydro-2H-pyran-2-yloxy)methyl]benzonitrile (Intermediate 26; 0.76 g, 3.5 mmol) in EtOH (2 mL) was added dropwise; the reaction mixture became clear. It was stirred at RT overnight. The crude obtained was purified by column chromatography with CH2Cl2 (A) and CH2Cl2/MeOH (95:5) (B) as eluents (0% to 80% B). The appropriate fractions were collected and the solvent removed to afford 1.25 g of sticky oil with some solids. It was dissolved in EtOAc/H2O (1:1, 150 mL). The organic layer was washed again with H2O (50 mL) and brine. It was dried over sodium sulphate, filtered and evaporated to afford the title compound (840 mg, 95%) as sticky oil.

Workup

  1. customA white precipitate formed
  2. stirringIt was stirred at RT overnight
  3. customThe crude obtained
  4. customwas purified by column chromatography with CH2Cl2 (A) and CH2Cl2/MeOH (95:5) (B) as eluents (0% to 80% B)
  5. customThe appropriate fractions were collected
  6. customthe solvent removed

Sources & evidence

ORD record
ord-fb0731c8b34b4f6589252f748a52b69f
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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