4-Methylmorpholine → HCID 131716239, compound

HRID 329740Notes

Reaction equation

HRID 329740 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.CN1CC[O:14]CC1.[Cl:17][C:18]1[CH:19]=[C:20]([C:39](Cl)=[O:40])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22]=2[CH:38]=1>C(Cl)(Cl)Cl>[OH2:14].[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([C:39]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:40])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22]=2[CH:38]=1.[Cl:17][C:18]1[CH:19]=[C:20]([C:39]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:40])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22]=2[CH:38]=1.[ClH:17]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 53846966HCID 53846966, compound

Product 1

HCID 131716239HCID 131716239, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.50 g of 3-aminoquinuclidine and 1.3 g of N-methylmorpholine in 30 ml of chloroform is added a solution of 4.5 g of 6-chloro-3,4-dihydro-2-methyl-3-oxo-4-(3-phenylpropyl)-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 purified with column chromatography using chloroform as an eluent and treated with ethanolic hydrochloric acid to give 6-chloro-3,4-dihydro-2-methyl-3-oxo-4-(3-phenylpropyl)-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride hemihydrate, melting at 274°-277° 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 purified with column chromatography
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-98154b6f5ade4a88aa18e68a6e3f1eda
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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