Dichloromethane → HCID 20026881, compound

HRID 1722599Notes

Reaction equation

HRID 1722599 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:23])[NH:10]2)=[O:4].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH:33]([NH2:35])[CH3:34])=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+].C(Cl)[Cl:42]>CN(C)C=O>[ClH:42].[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:5]([C:3](=[O:4])[CH2:2][NH:35][CH:33]([CH3:34])[CH2:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:23])[CH:8]=[CH:7]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31721(+-)-p-MethoxyamphetamineHCID 516892Sodium BicarbonateHCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Product 1

HCID 20026881HCID 20026881, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.72 g of 5-bromoacetyl-8-benzyloxycarbostyril, 3.3 g of N-(2-(p-methoxyphenyl)-1-methylethyl)amine, 2.6 g of sodium bicarbonate, 10 ml of methylene chloride and 2 ml of dimethylformamide is refluxed for 30 minutes under stirring. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chloroform, and the extract is washed with 10% hydrochloric acid, dried and then concentrated under reduced pressure to remove solvent. The residue is rcrystallized form a mixture of ethanol and isopropanol. 3.53 g of 8-benzyloxy-5-{1-oxo-2-[N-(2-(p-methoxypheyl)-1-methylethyl)amino]ethyl}carbostyril hydrochloride are obtained as colorless needles. Yield: 71.6%

Workup

  1. temperatureis refluxed for 30 minutes
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. extractionThe residue is extracted with chloroform
  5. washthe extract is washed with 10% hydrochloric acid
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. additiona mixture of ethanol and isopropanol

Sources & evidence

ORD record
ord-cef943cdbcf946be86e46cc609d8e439
Source dataset
uspto-grants-1989_08
Patent number
USRE033024

Reaction notes

Loading…