Sodium Iodide → 1-[4-(Methylsulfonyl)benzyl]homopiperazine
Reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl.N1CCCNCC1.[I-].[Na+].[CH3:19][S:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(O)C>[CH3:19][S:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:25][CH:24]=1)(=[O:21])=[O:22]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 120 mg of homopiperazine, 216 mg of homopiperazine dihydrochloride salt, 3 mL of ethanol was heated to 70° C. into a solution. To this solution were added sequentially 383 mg of sodium iodide and 250 mg of 4-(methylsulfonyl)benzyl bromide, followed by stirring at 70° C. for 14 hours. After the solution was cooled to room temperature, ethanol was removed under reduced pressure and 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 aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 176 mg of 1-[4-(methylsulfonyl)benzyl]homopiperazine.
Workup
- temperatureAfter the solution was cooled to room temperature
- customethanol was removed under reduced pressure and 20 mL of aqueous 2N sodium hydroxide
- additionwas added
- extractionthe mixture was extracted with 20 mL×2 of ethyl acetate
- washwashed with 20 mL of aqueous saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-de6286b21d5943d5a28510eaf4308cce
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686353B1
Reaction notes
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