Sodium Iodide → 1-(3,3-Diphenyipropyl)homopiperazine

HRID 2119341Notes

Reaction equation

HRID 2119341 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl.N1CCCNCC1.[I-].[Na+].CS(O[CH2:24][CH2:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)=O>C(O)C>[C:27]1([CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:25][CH2:24][N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 68163Hexahydro-1,4-diazepineHCID 222382923,3-Diphenylpropyl methanesulfonateHCID 23441047Homopiperazine dihydrochloride

Product 1

HCID 234410351-(3,3-Diphenyipropyl)homopiperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 120 mg of homopiperazine, 206 mg of homopiperazine dihydrochloride, and 3 mL of ethanol was heated to 70° C. to prepare a solution. 375 mg of sodium iodide and 287 mg of 3,3-diphenylpropyl methanesulfonate were added sequentially to the solution and the mixture was stirred at 70° C. for 14 hours. The mixture was allowed to cool to room temperature and the ethanol was removed under reduced pressure, followed by adding 20 mL of 2N aqueous sodium hydroxide solution and extracting 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, and concentrated to give 1-(3,3-diphenylpropyl)homopiperazine.

Workup

  1. customto prepare a solution
  2. temperatureto cool to room temperature
  3. customthe ethanol was removed under reduced pressure
  4. additionby adding 20 mL of 2N aqueous sodium hydroxide solution
  5. extractionextracting with 20 mL×2 of ethyl acetate
  6. washwashed with 20 mL of saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f782878f98cb4851a734eb12465d99b7
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

Loading…