1-METHANESULFONYL-PIPERAZINE

White solid

Step 2: 1-(methylsulfonyl)piperazineA mixture of tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate (1.0 g, 3.79 mmol) and TFA (0.86 g, 7.58 mmol) in CHTo a solution of test-butyl 4-(METHYLSULFONYL) PIPERAZINE-1-CARBOXYLATE (0.80 g, 3.0 MMOL) in CH2CI2 (10 ML) was added TFA (1 mL). The mixture was stirred at rt for 3 h before the volatiles were removed. ET20 was added to the residue then removed in vacuo to provide a yellow residue. ET20 was added and the mixture was sonicated. The white solid precipitate was filtered, washed with ET20, and dried in an oven to provide 530 mg of an off-white SOLID (64percent). 1H-NMR (DMSO-D6) 6 9.06 (s, 2H), 3.34-3. 31 (m, 4H), 3.21-3. 18 (m, 4H), 2.98 (s, 3H). LCMS [M+H] + = 165. 1.To a solution of fe/f-butyl 4-(methylsulfonyl)piperazine-1-carboxylate (0.80 g, 3.0mmol) in CHStep 1.To a stirred solution of 100.0 g (1.16 mol) of piperazine dissolved in 2000 ml of methylene chloride, was added drop wise of 133.2 g (1.16 mol) of methanesulfonyl chloride at 25-30°C . When addition was complete, the reaction mixture was stirred for 16 hrs. and mass was basified with 25percent w/v aqueous sodium hydroxide. The reaction mass was filtered and washed with 800 ml of water, and dried over anhydrous sodium sulfate. The methylene chloride was removed by distillation under vacuum to give 81.2 g (42.5 percent) as an off white solid with 98.3percent purity by chemical assay. Piperazine (4.9g, 0. 057MOL) was dissolved in DICHLOROMETHANE (100ML). Methanesulfonyl chloride (0.85mL, 0.011 mol) was added dropwise to the solution at room temperature. The reaction was stirred for 30 minutes. After this time 1 N potassium hydroxide (200mL) was added. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product, without further purification, as a solid (1. 07g, 11percent). 1H NMR (CDCI3, 300 MHz) 1.75 (s, 1H), 2.78 (s, 3H), 2.97 (m, 4H), 3.20 (m, 4H). MS: calculated : 164.06, found: 165.1.Piperazine (4.9 g, 0.057 mol) was dissolved in dichloromethane (100 mL). Methanesulfonyl chloride (0.85 mL, 0.011 mol) was added dropwise to the solution at room temperature. The reaction was stirred for 30 minutes. After this time IN potassium hydroxide (200 mL) was added. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product, without further purification, as a solid (1.07 g, 11percent). [1281] ^ NMR (CDC13, 300 MHz) 1.75 (s, 1H), 2.78 (s, 3H), 2.97 (m, 4H), 3.20 (m, 4H).[1282] MS: calculated: 164.06, found: 165.1.Piperazine (4.9 g, 0.057 mol) was dissolved in dichloromethane (100 mL). Methanesulfonyl chloride (0.85 mL, 0.011 mol) was added dropwise to the solution at room temperature. The reaction was stirred for 30 minutes. After this time 1 N potassium hydroxide (200 mL) was added. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product, without further purification, as a solid (1.07 g, 11percent).

Molecular Weight:164.23
XLogP3:-1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:164.06194880
Monoisotopic Mass:164.06194880
Topological Polar Surface Area:57.8
Heavy Atom Count:10
Complexity:188
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes