4-Methylmorpholine → HCID 19871159, compound

HRID 329736Notes

Reaction equation

HRID 329736 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.[CH2:17]([N:24]1[C:29]2[CH:30]=[C:31]([Cl:37])[CH:32]=[C:33]([C:34]([Cl:36])=[O:35])[C:28]=2[O:27][C:26](CC)([CH3:38])[C:25]1=[O:41])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[ClH:36].[CH2:17]([N:24]1[C:29]2[CH:30]=[C:31]([Cl:37])[CH:32]=[C:33]([C:34]([NH:1][CH:2]3[CH:7]4[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]4)[CH2:3]3)=[O:35])[C:28]=2[O:27][CH:26]([CH3:38])[C:25]1=[O:41])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1232383-AminoquinuclidineHCID 54116011HCID 54116011, compound

Product 1

HCID 19871159HCID 19871159, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.09 g of 3-aminoquinuclidine and 0.9 g of N-methylmorpholine in 20 ml of chloroform is added a solution of 3.25 g of 4-benzyl-6-chloro-2-ethyl-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 at room temperature 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 ethanolisopropyl ether and treated with ethanolic hydrochloric acid to give 4-benzyl-6-chloro-3,4-dihydro-2-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 267°-270° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. stirringby stirring at room temperature 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 ethanolisopropyl ether
  7. additiontreated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-6b2aac8d46b543ee8f1cb1974a6c0fee
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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