4-Methylmorpholine → HCID 14719852, compound

HRID 329737Notes

Reaction equation

HRID 329737 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.[Br:17][C:18]1[CH:19]=[C:20]([C:31](Cl)=[O:32])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[C:22]=2[CH:30]=1>C(Cl)(Cl)Cl>[Br:17][C:18]1[CH:19]=[C:20]([C:31]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:32])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[C:22]=2[CH:30]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 54260624HCID 54260624, compound

Product 1

HCID 14719852HCID 14719852, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.6 g of 3-aminoquinuclidine and 1.35 g of N-methylmorpholine in 25 ml of chloroform is added a solution of 4.0 g of 6-bromo-3,4-dihydro-2,4-dimethyl-3-oxo -2H-1,4-benzoxazine-8-carboxylic acid chloride in 20 ml of chloroform under cooling and stirring followed by stirring at room temperature for 3 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 to give 6-bromo-3,4-dihydro-2,4-dimethyl-3-oxo-N-(3-quinuclidinyl) -2H-1,4-benzoxazine-8-carboxamide, melting at 287°-288° C.

Workup

  1. temperatureunder cooling
  2. stirringby stirring at room temperature for 3 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

Sources & evidence

ORD record
ord-5d2fb09602204dcea53324f93cf492ab
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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