Hydrochloric Acid → HCID 13910858, compound

HRID 845396Notes

Reaction equation

HRID 845396 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[ClH:28]>O>[ClH:1].[ClH:28].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 13752589HCID 13752589, compound

Product 1

HCID 13910858HCID 13910858, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 16 g of 2-chloro-4-(4-fluorophenyl)quinoline and 25.4 g of 1-(2-hydroxyethyl)piperazine is stirred at 130° C. for 3 hours. After cooling, water is added and the resulting mixture is extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel (150 g) with chloroform - methanol (100 : 1). The eluates pooled are concentrated to give an oily residue, which is treated with ethanolic hydrogen chloride to afford the hydrochloride. Recrystallization from ethanol - ethyl acetate gives 16.7 g of the title compound, m.p. 210°-218° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel (150 g) with chloroform - methanol (100 : 1)
  6. concentrationThe eluates pooled are concentrated
  7. customto give an oily residue, which

Sources & evidence

ORD record
ord-34ff8048941d4cb39398223bbcdc6a01
Source dataset
uspto-grants-1988_07
Patent number
US04758566

Reaction notes

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