1-(1-Naphthyl)piperazine → HCID 21196263, compound

HRID 365365Notes

Reaction equation

HRID 365365 reaction equation
[C:1]1([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]([CH:29]=1)=[N:25][C:26](=[O:28])[N:27]=2.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[C:1]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]4[C:24]([CH:29]=3)=[N:25][C:26](=[O:28])[N:27]=4)[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 22464412HCID 22464412, compound

Product 1

HCID 21196263HCID 21196263, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet were added 2.64 grams (12.4 mmol) of N-(1-naphthyl)-piperazine, 3.0 grams (12.4 mmol) of 6-(2-bromoethyl)-benzimidazolone, 1.31 grams (12.4 mmol) sodium carbonate, 50 ml methylisobutylketone, and a catalytic amount of sodium iodide. The reaction was refluxed for 3 days, cooled, and evaporated to a brown gum. The gum was partitioned between 50 ml water and 75 ml ethyl acetate, and the ethyl acetate layer washed with brine, dried over sodium sulfate, and evaporated, then chromatographed on silica gel. Fractions containing the product were combined and evaporated, the residue taken up in tetrahydrofuran, treated with hydrochloric acid gas, and the resulting hydrochloride salt of the product filtered off to give a white solid, m.p. 260-262° C., 716 mg (14% yield).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet
  2. temperatureThe reaction was refluxed for 3 days
  3. temperaturecooled
  4. customevaporated to a brown gum
  5. customThe gum was partitioned between 50 ml water and 75 ml ethyl acetate
  6. washthe ethyl acetate layer washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customchromatographed on silica gel
  10. additionFractions containing the product
  11. customevaporated
  12. additiontreated with hydrochloric acid gas
  13. filtrationthe resulting hydrochloride salt of the product filtered off
  14. customto give a white solid, m.p. 260-262° C., 716 mg (14% yield)

Sources & evidence

ORD record
ord-6f3584d07cc7478e80d5a083b4128c00
Source dataset
uspto-grants-2000_10
Patent number
US06127373

Reaction notes

Loading…