4-Methylmorpholine → HCID 19871177, compound

HRID 329741Notes

Reaction equation

HRID 329741 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:38](Cl)=[O:39])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:22]=2[CH:37]=1>C(Cl)(Cl)Cl>[OH2:14].[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([C:38]([NH:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[O:39])[C:21]2[O:26][CH:25]([CH3:27])[C:24](=[O:28])[N:23]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:22]=2[CH:37]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 53848614HCID 53848614, compound

Product 1

HCID 19871177HCID 19871177, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.80 g of 3-aminoquinuclidine and 1.5 g of N-methylmorpholine in 3 ml of chloroform is added a solution of 5.0 g of 6-chloro-4-(4-fluorobenzyl)-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 purified with column chromatography using chloroform as an eluent and treated with ethanolic hydrochloric acid to give 6-chloro-4-(4-fluorobenzyl)-3,4-dihydro-2-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride monohydrate, melting at 117°-119° 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-1218d4b1089d4302ae323c970e4facfa
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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