Hydrochloric Acid → HCID 14233145, compound

HRID 1380137Notes

Reaction equation

HRID 1380137 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([O:34]C(=O)C)[CH2:21][NH:22][CH:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C>CO.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:34])[CH2:21][NH:22][CH:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 20026884HCID 20026884, compound

Product 1

HCID 14233145HCID 14233145, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

0.5 g of 8-benzyloxy-5-{1-acetoxy-2-[N-(2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril (α-isomer) hydrochloride.methanol is dissolved in a mixture of 10 ml of methanol and 2 ml of water, and 180 mg of triethylamine are added thereto. The mixture is refluxed for 5 hours under stirring. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chloroform, and the extract is washed with 5% hydrochloric acid. The chloroform solution is dried and concentrated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of isopropanol and ether. 365 mg of 8-benzyloxy-5-{1-hydroxy-2-[N-(2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril (α-isomer) hydrochloride are obtained. Yield: 86.1%

Workup

  1. additionare added
  2. temperatureThe mixture is refluxed for 5 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto remove solvent
  5. extractionThe residue is extracted with chloroform
  6. washthe extract is washed with 5% hydrochloric acid
  7. dry with materialThe chloroform solution is dried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is recrystallized from a mixture of isopropanol and ether

Sources & evidence

ORD record
ord-3498ee226db54d7c87c764495a5eb76d
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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