Potassium Carbonate → HCID 12751792, compound

HRID 1577935Notes

Reaction equation

HRID 1577935 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+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:37]=[C:38]([O:40][CH3:41])[CH:39]=1)[O:33][CH2:34][CH2:35][NH2:36]>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][NH:36][CH2:35][CH2:34][O:33][C:32]2[CH:37]=[C:38]([O:40][CH3:41])[CH:39]=[C:30]([O:29][CH3:28])[CH:31]=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 11430Potassium CarbonateHCID 12298898Ethanamine, 2-(3,5-dimethoxyphenoxy)-HCID 20570384HCID 20570384, compound

Product 1

HCID 12751792HCID 12751792, compoundYield 24.4%

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 30 ml of methanol. 0.5 g of anhydrous potassium carbonate and 1.4 g of 2-(3,5-dimethoxyphenoxy)ethylamine were added to the solution, and the resulting mixture was refluxed while stirring for 8 hours. The methanol was evaporated under reduced pressure, and the residue was rendered acidic with hydrochloric acid followed by washing with ethyl acetate. The hydrochloric acid layer was separated, extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residue was recrystallized from methanol-diethyl ether to obtain 0.4 g of 8-(2-propynyloxy)-5{3-[2-(3,5-dimethoxyphenoxy)ethylamino]-2-hydroxypropoxy}-3,4-dihydrocarbostyril hydrochloride having a melting point of 187°-189° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. customThe methanol was evaporated under reduced pressure
  3. washby washing with ethyl acetate
  4. customThe hydrochloric acid layer was separated
  5. extractionextracted with chloroform
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe chloroform was evaporated under reduced pressure
  9. customthe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-567bde1289c04d2a80cf5e4682a40099
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

Loading…