4-Methylmorpholine → HCID 19871166, compound

HRID 329744Notes

Reaction equation

HRID 329744 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.[CH3:17][N:18]1[C:23]2[CH:24]=[C:25]([CH3:31])[CH:26]=[C:27]([C:28]([Cl:30])=[O:29])[C:22]=2[O:21][CH2:20][C:19]1=[O:32]>C(Cl)(Cl)Cl>[ClH:30].[CH3:17][N:18]1[C:23]2[CH:24]=[C:25]([CH3:31])[CH:26]=[C:27]([C:28]([NH:1][CH:2]3[CH:7]4[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]4)[CH2:3]3)=[O:29])[C:22]=2[O:21][CH2:20][C:19]1=[O:32]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 53844240HCID 53844240, compound

Product 1

HCID 19871166HCID 19871166, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.56 g of 3-aminoquinuclidine and 2.16 g of N-methylmorpholine in 40 ml of chloroform is added a solution of 4.72 g of 3,4-dihydro-4,6-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride in 20 ml of chloroform under cooling and stirring followed by stirring 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 purified with column chromatography using chloroform as an eluent and treated with ethanolic hydrochloric acid to give 3,4-dihydro-4,6-dimethyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 283°-284° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. stirringby stirring 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 purified with column chromatography
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-20b865b49e7e4b45b6e9e148e423b277
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

Loading…