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

HRID 218326Notes

Reaction equation

HRID 218326 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-051fafa876604feda7ee4587912fbbc2
Source dataset
uspto-grants-2012_06
Patent number
US08198437B2

Reaction notes

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