Diethylamine → HCID 18958811, compound

HRID 1708365Notes

Reaction equation

HRID 1708365 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].CN1CCCC1=O>[Cu](I)I.[Cu].O>[ClH:1].[CH2:14]([N:16]([CH2:17][CH3:18])[C:2]1[C:11]2[C:6](=[C:7]([CH3:12])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1)[CH3:15]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 3450912HCID 3450912, compound

Product 1

HCID 18958811HCID 18958811, compound

Reagents, catalysts & solvents 2

HCID 59592044HCID 59592044, compoundCatalystHCID 962WaterSolvent

Procedure

2.0 Grams of 4-chloro-8-methylcarbostyril, 5 ml of diethylamine, 0.2 g of copper iodide-copper powder mixture and 20 ml of N-methylpyrrolidone were placed in an autoclave and heated at 180°-190° C. for 10 hours. To the reaction mixture was added water, then extracted with ethyl acetate. The extract was washed with water, dried, and the solvent was removed by evaporation. The residue thus obtained was purified by a silica gel column chromatography (eluent: dichloromethane). The product was converted into hydrochloride by using ethanol-HCl, and recrystallized from acetone-diethyl ether to obtain 0.6 g of 4-diethylamino-8-methylcarbostyril hydrochloride. Light brown powdery substance. Melting point: 183°-186° C.

Workup

  1. temperatureheated at 180°-190° C. for 10 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was removed by evaporation
  6. customThe residue thus obtained
  7. customwas purified by a silica gel column chromatography (eluent: dichloromethane)
  8. customrecrystallized from acetone-diethyl ether

Sources & evidence

ORD record
ord-b0d7d573fc6c491b9ae3b9ad2e8ad9c7
Source dataset
uspto-grants-1994_10
Patent number
US05358949

Reaction notes

Loading…