Potassium Carbonate → HCID 70279053, compound

HRID 2393271Notes

Reaction equation

HRID 2393271 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[CH:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:3]1.[CH3:19][C:20]1([CH3:26])[CH2:25][NH:24][CH2:23][CH2:22][NH:21]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5]([C@H:4]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH2:3][C@H:2]2[N:24]2[CH2:23][CH2:22][NH:21][C:20]([CH3:26])([CH3:19])[CH2:25]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13154759HCID 13154759, compoundHCID 146641862,2-Dimethylpiperazine

Product 1

HCID 70279053HCID 70279053, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1,6-dichloro-3-(4-fluorophenyl)-2,3-dihydro-1H-indene (28 g, 0.1 mol), 2,2-dimethylpiperazine (15 g, 0.13 mol) and potassium carbonate (30 g) in acetone (250 mL) was refluxed for 18 h. The reaction mixture was evaporated in vacuo and treated with water and ether. The ether phase was separated and extracted with 1M methane sulfonic acid. The base was liberated with 10M sodium hydroxide, extracted with ether and dried (MgSO4). After filtration and evaporation in vacuo the residue was dissolved in acetone and treated with fumaric acid. The fumarate salt was filtered to give 27 g of 1 as the hemifumarate salt, mp 240°-241° C. A sample recrystallized from ethanol had mp 242°-244° C. Isomeric purity (TLC): 95% trans isomer (racemate).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe reaction mixture was evaporated in vacuo
  3. additiontreated with water and ether
  4. customThe ether phase was separated
  5. extractionextracted with 1M methane sulfonic acid
  6. extractionextracted with ether
  7. dry with materialdried (MgSO4)
  8. filtrationAfter filtration and evaporation in vacuo the residue
  9. dissolutionwas dissolved in acetone
  10. additiontreated with fumaric acid
  11. filtrationThe fumarate salt was filtered

Sources & evidence

ORD record
ord-4d9b6da47e2d4a94bc4a34746442c2de
Source dataset
uspto-grants-1998_09
Patent number
US05807855

Reaction notes

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