4-Nitroaniline → HCID 13084725, compound

HRID 1462559Notes

Reaction equation

HRID 1462559 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:21]([C:24]1[CH:30]=[CH:29][C:27](N)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>COC(C)CCO.[Cu]>[N+:21]([C:24]1[CH:30]=[CH:29][C:27]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][CH2:9][C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH2:2][CH2:3]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 74754-NitroanilineHCID 11430Potassium CarbonateHCID 15591352HCID 15591352, compound

Product 1

HCID 13084725HCID 13084725, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 172913-Methoxy-1-butanolSolvent

Procedure

2.87 Grams of 6-(3-piperazinylpropyl)-3,4-dihydrocarbostyril, 2.0 g of p-nitroaniline, 0.8 g of potassium carbonate and 0.2 g of copper powder were mixed in 80 ml of 3-methoxybutanol and refluxed by heating for 5 hours. Then 3 g of activated carbon was added to the reaction mixture and filtered with Celite, then the mother liquor was concentrated under a reduced pressure to obtain a residue. The residue was purified by a silica-gel chromatography and recrystallized from isopropanol to obtain 0.55 g of 6-{3-[4-(4-nitrophenyl)-1-piperazinyl]propyl}-3,4-dihydrocarbostyril in yellow needle-like crystals, having the melting point of 189°-192° C.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 5 hours
  3. additionThen 3 g of activated carbon was added to the reaction mixture
  4. filtrationfiltered with Celite
  5. concentrationthe mother liquor was concentrated under a reduced pressure
  6. customto obtain a residue
  7. customThe residue was purified by a silica-gel chromatography
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f1f3098283d640fdb206e3f7b91d84e7
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

Loading…