Triethylamine → HCID 19607855, compound

HRID 1603114Notes

Reaction equation

HRID 1603114 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([Cl:38])[CH:37]=1)[C:32](Cl)=[O:33]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:32](=[O:33])[C:31]3[CH:30]=[C:29]([Cl:28])[CH:37]=[C:36]([Cl:38])[CH:35]=3)=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 761913,5-Dichlorobenzoyl chloride2×HCID 19607823HCID 19607823, compound

Product 1

HCID 19607855HCID 19607855, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Fluoro-1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (0.15 g) is dissolved in dichloromethane (10 ml) and thereto is added triethylamine (0.31 ml). To the mixture is added dropwise a solution of 3,5-dichlorobenzoyl chloride (0.14 g) in dichloromethane (2.0 ml) under ice-cooling, and the mixture is stirred for 30 minutes under ice-cooling, and further, at room temperature for 1 hour. To the mixture are added triethylamine (0.31 ml) and 3,5-dichlorobenzoyl chloride (0.14 ml). The mixture is stirred at room temperature for 4 hours. The reaction mixture is washed with water, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:5→1:4), and recrystallized from ethyl acetate/n-hexane to give 6-fluoro-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.12 g) and 6-fluoro-1-{4-[bis-(3,5-dichlorobenzoyl)amino]benzoyl}-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfurther, at room temperature for 1 hour
  4. stirringThe mixture is stirred at room temperature for 4 hours
  5. washThe reaction mixture is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:5→1:4)
  9. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-fb700929d42a4dff86992cc8ac823d78
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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