Hydrochloric Acid → HCID 14198563, compound

HRID 2231220Notes

Reaction equation

HRID 2231220 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:3]1=2.[Cl:17][CH2:18][CH2:19][CH2:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl>C(C(C)=O)C.C(OCC)(=O)C>[ClH:17].[O:2]1[CH:6]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][C:21](=[O:29])[C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH2:13][CH2:12]3)[C:3]1=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 197503-(4-Fluorobenzoyl)propyl chloride2×HCID 14198541HCID 14198541, compound

Product 1

HCID 14198563HCID 14198563, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.5 Mmol (1.79 g) of 1-benzo[b]furan-7-yl-piperazine HCl, together with 9.1 mmol (1.82 g) of 1-chloro-3-(4-fluorobenzoyl)-propane, 20 mmol (2.80 g) of potassium carbonate and a catalytic quantity (approximately 100 mg) of sodium iodide as a suspension in 50 ml of methyl ethyl ketone, was heated with thorough stirring so that the solvent refluxes. After stirring for 16 hours, 9.1 mmol of 1-chloro-3-(4-fluorobenzoyl)propane and 20 mmol of potassium carbonate were added again. After stirring for another 16 hours at reflux temperature, cooling, filtering and evaporating to dryness in vacuo were carried out. The residue was chromatographed on silica gel with ethyl acetate as an eluent. After evaporating the fractions which comprised the desired product, material was obtained which was converted into the title compound via treatment with 1 equivalent of a HCl solution in ethyl acetate.

Workup

  1. stirringAfter stirring for 16 hours
  2. stirringAfter stirring for another 16 hours
  3. temperatureat reflux temperature
  4. temperaturecooling
  5. filtrationfiltering
  6. customevaporating to dryness in vacuo
  7. customThe residue was chromatographed on silica gel with ethyl acetate as an eluent
  8. customAfter evaporating the fractions which
  9. custommaterial was obtained which

Sources & evidence

ORD record
ord-382e6d87adc549fc93e19f736529c4c3
Source dataset
uspto-grants-1988_11
Patent number
US04782061

Reaction notes

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