4-Methylmorpholine → HCID 19871181, compound

HRID 329743Notes

Reaction equation

HRID 329743 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:41](Cl)=[O:42])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[C:22]=2[CH:40]=1>C(Cl)(Cl)Cl>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([C:41]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:42])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=3)[C:22]=2[CH:40]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 54057876HCID 54057876, compound

Product 1

HCID 19871181HCID 19871181, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.35 g of 3-aminoquinuclidine and 1.14 g of N-methylmorpholine in 30 ml of chloroform is added a solution of 4.5 g of 6-chloro-4-(3-trifluoromethylbenzyl)-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride in 20 ml of chloroform under cooling and stirring followed by stirring for 4 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 and treated with ethanolic hydrochloric acid to give 6-chloro-4-(3-trifluoromethylbenzyl)-3,4-dihydro-2-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 271°-274° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. stirringby stirring for 4 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
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-99e19c1c5abb4a2cb191e3bcfb41afea
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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