Morpholine → Morpholine-4-carboxamide

HRID 2233012Notes

Reaction equation

HRID 2233012 reaction equation
ClC1C=C(C=[CH:9][N:10]=1)C(O)=O.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=[O:21].C(=O)(O)[O-].[Na+]>CCOC(C)=O>[N:11]1([C:9]([NH2:10])=[O:21])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 111923Propylphosphonic anhydrideHCID 2369852-Chloroisonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 75088Morpholine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 315 mg of 2-chloroisonicotinic acid and 209 mg of morpholine in EtOAc (4.0 mL) was stirred as 1.27 g of a 50% solution of 1-propanephosphonic acid cyclic anhydride was added. This mixture was stirred at room temperature for six h. and another 1.27 g of the anhydride was added followed by stirring for another 18 h. The reaction was poured into saturated sodium bicarbonate solution and extracted with EtOAc (3×). The organic layers were dried over sodium sulfate, filtered, and concentrated to provide the morpholine amide.

Workup

  1. additionwas added
  2. stirringby stirring for another 18 h
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a458a593b4f440599fae9e7e845eeb3d
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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