Hydrochloric Acid → 8-(2-Propynyloxy)-5-[3-(t-butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril hydrochloride

HRID 1577933Notes

Reaction equation

HRID 1577933 reaction equation
[O:1]1[CH2:20][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[CH:18])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:19])[NH:10]2.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].[ClH:26].Cl.C(O)C>CO>[ClH:26].[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:20][NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:11]=1[NH:10][C:9](=[O:19])[CH2:8][CH2:7]2)[C:17]#[CH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 127517465-(2,3-Epoxypropoxy)-8-(2-propynyloxy)-3,4-dihydrocarbostyrilHCID 21887872Ethanol hydrochloride

Product 1

HCID 127517858-(2-Propynyloxy)-5-[3-(t-butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 g of 5-(2,3-epoxypropoxy)-8-(2-propynyloxy)-3,4-dihydrocarbostyril was dissolved in 15 ml of methanol, and 2.6 g of t-butylamine was added to the solution, followed by allowing the mixture to stand at 15°-20° C. for 12 hours. After completion of the reaction, the methanol and the t-butylamine were evaporated under reduced pressure, and the resulting crude oil was converted into the hydrochloride thereof using hydrochloric acid and ethanol. The solvent was evaporated under reduced pressure, and the resulting crystals were dissolved in water and washed with chloroform to remove impurities. The aqueous layer was made alkaline with sodium hydroxide and then extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure to obtain colorless crystals, which were converted into the hydrochloride thereof with hydrochloric acid-ethanol. The solvent was evaporated under reduced pressure, and the residue was recrystallized from isopropanol to obtain 1.6 g of 8-(2-propynyloxy)-5-[3-(t-butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril hydrochloride having a melting point of 182°-183° C.

Workup

  1. customAfter completion of the reaction
  2. customthe methanol and the t-butylamine were evaporated under reduced pressure
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe resulting crystals were dissolved in water
  5. washwashed with chloroform
  6. customto remove impurities
  7. extractionextracted with chloroform
  8. washThe chloroform layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe chloroform was evaporated under reduced pressure
  11. customto obtain colorless crystals, which
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-c5415178362e4d04b7b0f1c216afb3c0
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

Loading…