4-Methylmorpholine → Y 25130

HRID 329735

Reaction equation

HRID 329735 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:30](Cl)=[O:31])[C:21]2[O:26][CH2:25][C:24](=[O:27])[N:23]([CH3:28])[C:22]=2[CH:29]=1>C(Cl)(Cl)Cl>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([C:30]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:31])[C:21]2[O:26][CH2:25][C:24](=[O:27])[N:23]([CH3:28])[C:22]=2[CH:29]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 299420066-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carbonyl chloride

Product 1

HCID 115000Y 25130

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.0 g of 3-aminoquinuclidine and 3.0 g of N-methylmorpholine in 60 ml of chloroform is added 6.2 g of 6-chloro-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 ethanol-isopropyl ether and treated with ethanolic hydrochloric acid to give 6-chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 281° 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 ethanol-isopropyl ether
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-3fc083efb68e4fc1b6dec064cc9a1c77
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Linked notes

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