Ethanol → 4-Benzyl-N-hydroxymorpholine-2-carboximidamide

HRID 2063354Notes

Reaction equation

HRID 2063354 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl.[NH2:20][OH:21].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([NH2:15])=[N:20][OH:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 156511954-Benzylmorpholine-2-carbonitrile2×

Product 1

HCID 748942584-Benzyl-N-hydroxymorpholine-2-carboximidamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-benzylmorpholine-2-carbonitrile (intermediate 25, 5.0 g, 24.7 mmol) in the mixture of ethanol and water (2/1, 75 ml) was added hydroxylamine hydrochloride (5.2 g, 74.2 mmol) and sodium bicarbonate (13.1 g, 123.5 mmol), and the reaction mixture was stirred under reflux for 12 hours. The reaction was diluted with chloroform, and the reaction mixture was washed with water and brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The resulting 4-benzyl-N′-hydroxymorpholine-2-carboxamidine (intermediate 26) was used for next reaction without further purification.

Workup

  1. temperatureunder reflux for 12 hours
  2. washthe reaction mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting 4-benzyl-N′-hydroxymorpholine-2-carboxamidine (intermediate 26) was used for next reaction without further purification

Sources & evidence

ORD record
ord-1d3075c5056f46e6ab705a11f46f55dc
Source dataset
uspto-grants-2012_10
Patent number
US08288383B2

Reaction notes

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