Aniline → HCID 13568664, compound

HRID 231104Notes

Reaction equation

HRID 231104 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:18][CH2:19]Cl)[C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)=[O:6].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:22]1([N:21]2[CH2:19][CH2:18][N:4]([C:5]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]4)=[O:6])[CH2:3][CH2:2]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 14497707HCID 14497707, compound

Product 1

HCID 13568664HCID 13568664, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture consisting of 15.9 g of 6-[bis-(2-chloroethyl)aminocarbonyl]-3,4-dihydrocarbostyril, 5.5 g of aniline and 70 ml of methanol was refluxed for 15 hours. After cooled the reaction mixture, 3.06 g of sodium carbonate was added to the reaction mixture and the reaction mixture was further refluxed for 8 hours. The reaction mixture was cooled and crystals precipitated in the reaction mixture were collected by filtration, and recrystallized from isopropanol to obtain 6.3 g of 6-(4-phenyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 200°-201° C.

Workup

  1. temperaturewas refluxed for 15 hours
  2. additionwas added to the reaction mixture
  3. temperaturethe reaction mixture was further refluxed for 8 hours
  4. temperatureThe reaction mixture was cooled
  5. customcrystals precipitated in the reaction mixture
  6. filtrationwere collected by filtration
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-4075cfa0ae5742ceb61dbd9a47cef0ee
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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