4-Methylmorpholine → HCID 19871151, compound

HRID 329734Notes

Reaction equation

HRID 329734 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.CN1CCOCC1.[Cl:17][C:18]1[CH:19]=[C:20]([C:32](Cl)=[O:33])[C:21]2[O:26][CH:25]([CH2:27][CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:22]=2[CH:31]=1>C(Cl)(Cl)Cl>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([C:32]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:33])[C:21]2[O:26][CH:25]([CH2:27][CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:22]=2[CH:31]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 54407410HCID 54407410, compound

Product 1

HCID 19871151HCID 19871151, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.43 g of 3-aminoquinuclidine and 2.5 g of N-methylmorpholine in 50 ml of chloroform is added 5.2 g of 6-chloro-2-ethyl-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride under cooling and stirring followed by stirring for 2 hours. The resultant solution is washed with water, aqueous sodium hydrogen carbonate and then water, and dried over magnesium sulfate. After the solvent is distilled off under reduced pressure, the residue is recrystallized from ethanolisopropyl ether and treated with ethanolic hydrochloric acid to give 6-chloro-2-ethyl-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 295° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. stirringby stirring for 2 hours
  3. washThe resultant solution is washed with water, aqueous sodium hydrogen carbonate
  4. dry with materialwater, and dried over magnesium sulfate
  5. distillationAfter the solvent is distilled off under reduced pressure
  6. customthe residue is recrystallized from ethanolisopropyl ether
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-6cafa0ed97464edeb552cf6e83a58564
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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