Sodium Iodide → 1-(3,3-Diphenyipropyl)homopiperazine
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]=1Participants
6
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 126 mg of homopiperazine. 218 mg of homopiperazine dihydrochloride, 3 mL of ethanol was heated to 70° C. into a solution. 378 mg of sodium iodide and 289 mg of 3,3-diphenylpropyl methanesulfonate were added sequentially to the solution and the solution was stirred at 70° C. for 15 hours. After the solution was cooled to room temperature, the ethanol was removed under reduced pressure followed by adding 20 mL of aqueous 2N sodium hydroxide 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
- temperatureAfter the solution was cooled to room temperature
- customthe ethanol was removed under reduced pressure
- additionby adding 20 mL of aqueous 2N sodium hydroxide
- extractionextracting with 20 mL×2 of ethyl acetate
- washwashed with 20 mL of saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-582d173f66f941fdade00aa4f2ed9624
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686353B1
Reaction notes
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