Morpholine → Morpholine-4-carboxamide

HRID 1270145Notes

Reaction equation

HRID 1270145 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 hrs. and another 1.27 g of the anhydride was added followed by stirring for another 18 hrs. 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 hrs
  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-526ce919a13e4ef289962b60d7f4cb3a
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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