Morpholine → HCID 20332340, compound

HRID 2057452Notes

Reaction equation

HRID 2057452 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][Cl:20])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3].C(=O)([O-])[O-].[K+].[K+].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CO>[ClH:20].[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 20570384HCID 20570384, compound

Product 1

HCID 20332340HCID 20332340, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of 8-(2-propynyloxy)-5-(3-chloro-2-hydroxypropoxy)-3,4-dihydrocarbostyril was dissolved in 20 ml of methanol. 0.7 g of anhydrous potassium carbonate and 1.7 g of morpholine were then added to the solution followed by stirring while refluxing for 4 hours. After completion of the reaction, the methanol and the unreacted morpholine were evaporated under reduced pressure, and the residual oil was converted into a hydrochloride with an aqueous hydrochloric acid, and washed with chloroform. The aqueous layer was separated, made alkaline with sodium hydroxide and extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residue was converted into a hydrochloride with ehtanolhydrochloric acid. Recrystallization from water-ethanol gave 0.8 g of 8-(2-propynyloxy)-5-(2-hydroxy-3-morpholinopropoxy)-3,4-dihydrocarbostyril hydrochloride having a melting point of 234.5°-235° C.

Workup

  1. temperaturewhile refluxing for 4 hours
  2. customAfter completion of the reaction
  3. customthe methanol and the unreacted morpholine were evaporated under reduced pressure
  4. washwashed with chloroform
  5. customThe aqueous layer was separated
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe chloroform was evaporated under reduced pressure
  10. customRecrystallization from water-ethanol

Sources & evidence

ORD record
ord-1c6efd5b70e54f119a725d5fc68aef83
Source dataset
uspto-grants-1980_07
Patent number
US04210753

Reaction notes

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