Potassium Carbonate → 1-(3,3-Diphenylpropyl)-4-(2-quinolylmethyl)homopiperazine

HRID 2119348Notes

Reaction equation

HRID 2119348 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH2:12][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 234410351-(3,3-Diphenyipropyl)homopiperazine

Product 1

HCID 234410281-(3,3-Diphenylpropyl)-4-(2-quinolylmethyl)homopiperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The resulting 1-(3,3-diphenylpropyl)homopiperazine was dissolved in 3 mL of ethanol, mixed with 228 mg of 2-(chloromethyl)quinoline hydrochloride and 141 mg of potassium carbonate, and stirred at 70° C. for 14 hours. The mixture was cooled to room temperature and the ethanol was removed under reduced pressure, 20 mL of aqueous 2N sodium hydroxide was added and the mixture was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined, washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate/methanol 95:5), to obtain 109 mg of the titled compound. This was treated with a hydrogen chloride solution in ether and the solvent was removed under reduced pressure and the residue was dried to give the hydrochloride salt of the titled compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe ethanol was removed under reduced pressure, 20 mL of aqueous 2N sodium hydroxide
  3. additionwas added
  4. extractionthe mixture was extracted with 20 mL×2 of ethyl acetate
  5. washwashed with 20 mL of saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica gel, ethyl acetate/methanol 95:5)

Sources & evidence

ORD record
ord-1348f07392b945358084ad74d6d8309a
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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