Home Cart 0 Sign in  

[ CAS No. 27106-51-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 27106-51-0
Chemical Structure| 27106-51-0
Structure of 27106-51-0 * Storage: {[proInfo.prStorage]}

Quality Control of [ 27106-51-0 ]

Related Doc. of [ 27106-51-0 ]

SDS
Alternatived Products of [ 27106-51-0 ]
Alternatived Products of [ 27106-51-0 ]

Product Details of [ 27106-51-0 ]

CAS No. :27106-51-0 MDL No. :MFCD02018961
Formula : C11H16N2O2S Boiling Point : 387.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :240.32 g/mol Pubchem ID :-
Synonyms :

Safety of [ 27106-51-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 27106-51-0 ]

  • Downstream synthetic route of [ 27106-51-0 ]

[ 27106-51-0 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 110-85-0 ]
  • [ 98-59-9 ]
  • [ 27106-51-0 ]
YieldReaction ConditionsOperation in experiment
99.5% With triethylamine In benzene 1 EXAMPLE 1 SPC11 Piperazine 43 g (0.5 mol) and triethylamine 69 ml (0.55 mol) were dissolved with agitation in 600 ml of anhydrous benzene maintained at a temperature of 35°-40°C in a 3-liter flask. A solution of 19.06 g (0.1 mol) of p-toluenesulfonylchloride (Formula II) dissolved in 600 ml of anhydrous benzene was added dropwise into the amine solution over a period of about 2 hours with stirring. Stirring was continued until the precipitation of triethylamine-HCl ceased. The reaction mixture was filtered to remove the precipitate and then the filtrate was dried under reduced pressure, yielding a white powder. Stripping off unreacted piperazine by sublimation under reduced pressure (20 mm Hg) from the white powder gave a pale yellow powder which was recrystallized from benzene-petroleum ether (6: 4). 23.9 g of white plate crystals of p-toluenesulfonylpiperazine (Formula III) were obtained. The yield was 99.5% of p-toluenesulfonylchloride. Melting point: 108.5°~109.5°C. The IR spectrum in Nujol is shown in FIG. 1.
93% With acetic acid at 60℃; for 0.0666667h; Sonication; Irradiation;
91.2% With triethylamine In dichloromethane at 25℃; for 3h; 1.2 Step 2. Add 60g piperazine, 146.1g p-toluenesulfonyl chloride, 84.6g triethylamine and 397.5g dichloromethane to the reaction flask. The reaction temperature is 25°C and the time is 3h. TLC detects that the piperazine reaction is complete and quenched with water. The organic phase was washed twice with 60 g of water, and concentrated at 45°C until no droplets dripped out to obtain the compound of formula (IV) with a purity of 95.4% and a yield of 91.2%.
90% With triethylamine In dichloromethane at 0℃; for 0.5h;
83% With triethylamine In dichloromethane at 0℃; for 2h;
73% In N,N-dimethyl-formamide Inert atmosphere;
With 1,4-dioxane
With acetone
With triethylamine In chloroform at 1 - 20℃; for 3h; 13 1-Tosylpiperazine: According to scheme 1, step 1: Commercially available anhydrous piperazine (13.4 mmol) was dissolved in chloroform. To this solution, Triethylamine (13.4 mmol) was added, keeping the temperature 1 °C. Tosyl chloride (6.7 mmol) dissolved in chloroform (10 mL)was added slowly within two hours with stirring at 1 °C keeping the reaction condition dry. The reaction mixture was further stirred for one hour at room temperature. The reaction was over and solvent was evaporated under reduced pressure to get crude. The desired product 1-acetylpiperazine was obtained by column chromatography using chloroform- methanol as eluent. The compound 1 -tosylpiperazine was obtained as colourless oil.
2.1 g With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h; Inert atmosphere; 59.d Step d) Synthesis of 4-tolylsulfonylpiperazine (31, R2 =Me) [0142] To a stinedsolution of p-tolylsulfonyl chloride 31 (1.90g,10.0mmol)in methylene chloride (50 mL) at 0 °C was added piperazine (0.95 g, 11.0 mmol) and triethyl amine (1.1 g, 11.0mmol),.Themixturewasstined at 0 °C for 10 min and at room temperatureunder argon atmosphere for 2 h. After the completion of reaction, as monitored by TLC, mixture was diluted with water. The aqueouslayer was extractedwith methylene chloride, and the combined organiclayer was dried over MgS04. The solvent removedunder reduced pressureto give 2.1 g of 4-tolylsulfonylpiperazine as a white solid,used in next step without further purification.1H NMR (400 MHz, CDCh) 8 7.65 (d, 2H,J = 8.0 Hz); 7.43 (d, 2H,J = 8.0 Hz); 3.07 (m, 4H); 2.60-2.51 (m, 4H); 2.45 (s, 3H)
With triethylamine In dichloromethane at 0℃;
With triethylamine In dichloromethane at 0℃; for 0.5h;
In dichloromethane at 0 - 10℃; for 0.5h; General procedure for the synthesis of 1-((4-substituted-phenyl)sulfonyl)piperazine (2a-j) 4-substituted aryl sulfonyl chloride (10 mmol, 1 equiv) was added in one portion to a solution of piperazine (60 mmol, 6 equiv) in CH2Cl2 (10 mL) at 0 °C. The reaction mixture was stirred at 0-10 °C for 30 min. Dilute with more amount of CH2Cl2 (20 mL), and removed the excess piperazine by the addition of saturated NaHCO3 (aq) (50 mL). Separate the organic layer washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo to provide crude product. The crude product was used directly or purified by crystal-lization using methanol to yield pure 1-((4-substituted-phenyl)sulfonyl)piperazine.
In dichloromethane at 0℃; for 0.5h;
With triethylamine In dichloromethane at 0 - 20℃; for 4h; General procedure for preparation of sulfonamide EA derivatives General procedure: The synthesis of the key intermediates compounds 2(a-i), 3(a-i) as well as 4(a-i) were achieved following the previously reported procedures. Ethylene diamine sulfonyl 2(a-i) and piperaziene sulfonyl 3(a-i) were prepared according to references 48-53, while, the 4-aminopiperidine-1-sulfonyl 4(a-i) were prepared according to reference 55. To a solution of 1,2-diaminoethane or piperazine (5.00 mmol) in dichloromethane (10 mL), triethylamine (1.51 g, 2 mL, 15.00 mmol) were added with stirring. The mixture was cooled to 0°C and a solution of the appropriate sulfonyl chloride (2.50 mmol) in dichloromethane (2 mL) was added dropwise. The mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with 20 mL saturated aqueous solution of NaHCO3 and the organic layer was extracted with ethyl acetate (3x 20mL), dried over magnesium sulfate and concentrated under reduced pressure to give the desired intermediates 2(a-i) and 3(a-i). For the synthesis of intermediates 4(a-i), a solution of 4-(N-Boc) aminopiperidine (0.10 g, 0.50 mmol) in dichloromethane (10 mL) and triethylamine (0.15 g, 0.2 mL, 1.50 mmol) was added at 0°C. Then, a solution of sulfonyl chloride (0.50 mmol) in dichloromethane (2 mL) was added in small portions. The reaction was stirred for 4 hours, then, the reaction mixture was quenched with 20 mL of a saturated aqueous solution of NaHCO3. The aqueous layer was extracted with ethyl acetate (3x 20mL), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in solution (5 mL) of HCl in dioxane at room temperature for 1h. All solvents were removed under reduced pressure, which gave the corresponding crude salt. The intermediates 2(a-i), 3(a-i) and 4(a-i) were used in the next step directly without further purification. To a solution of EDC (0.62 g, 0.39 mmol), HOBt (0.60 g, 0.39 mmol) and ethacrynic acid (0.10 g, 0.33 mmol) in dry DMF (5 mL) at 0°C, crude amine (2(a-i) or 3(a-i)) was added. In the case of the intermediates 4(a-i), 0.30 mmol of triethylamine was used and the solution was stirred at room temperature. The reaction was monitored by TLC until all the amine was consumed. The mixture was diluted with ethyl acetate (100 mL) and extracted (3x 20mL). The organic phase was washed with water (2 × 50 mL) and brine (3 × 50 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography.
In acetonitrile Schlenk technique; Inert atmosphere;

Reference: [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD. - US3943135, 1976, A
[2]Location in patent: scheme or table Maurya, Ram Awatar; Hoang, Phan Huy; Kim, Dong-Pyo [Lab on a chip, 2012, vol. 12, # 1, p. 65 - 68]
[3]Current Patent Assignee: HUNAN JIUDIAN HONGYANG PHARMACY - CN111205247, 2020, A Location in patent: Paragraph 0024-0025
[4]Alvala, Mallika; Babu, Bathini Nagendra; Devi, Ganthala Parimala; Godugu, Chandraiah; Manasa, Kesari Lakshmi; Nagesh, Narayana; Sigalapalli, Dilep Kumar; Thatikonda, Sowjanya; Vuppaladadium, Sowmya [RSC Medicinal Chemistry, 2020, vol. 11, # 11, p. 1295 - 1302]
[5]Man, Ruo-Jun; Tang, Dan-Jie; Lu, Xiao-Yuan; Duan, Yong-Tao; Tao, Xiang-Xiang; Yang, Meng-Ru; Wang, Le-Le; Wang, Bao-Zhong; Xu, Chen; Zhu, Hai-Liang [MedChemComm, 2016, vol. 7, # 9, p. 1759 - 1767]
[6]Richter, Adrian; Narula, Gagandeep; Rudolph, Ines; Seidel, Rüdiger W.; Wagner, Christoph; Av-Gay, Yossef; Imming, Peter [ChemMedChem, 2022, vol. 17, # 6]
[7]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2436685, 1944, A
[8]Jacobi [Chemische Berichte, 1933, vol. 66, p. 113,116]
[9]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2014/122670, 2014, A1 Location in patent: Page/Page column 42
[10]Current Patent Assignee: NORTHEASTERN UNIVERSITY IN SHENYANG, CHINA; NORTHEASTERN UNIVERSITY IN BOSTON, MASSACHUSETTS - WO2016/14975, 2016, A2 Location in patent: Paragraph 0142
[11]Yin, Yong; Sha, Shao; Wu, Xun; Wang, She-Feng; Qiao, Fang; Song, Zhong-Cheng; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2019, vol. 182]
[12]Jadala, Chetna; Sathish, Manda; Anchi, Pratibha; Tokala, Ramya; Lakshmi, Uppu Jaya; Reddy, Velma Ganga; Shankaraiah, Nagula; Godugu, Chandraiah; Kamal, Ahmed [ChemMedChem, 2019, vol. 14, # 24, p. 2052 - 2060]
[13]Ramalingeswara Rao; Mohana Rao Katiki; Dileep Kommula; SaiShyam Narayanan; Ruby John Anto; Murty [Croatica Chemica Acta, 2019, vol. 92, # 3, p. 393 - 402]
[14]Alvala, Mallika; Angeli, Andrea; Manasa, Kesari Lakshmi; Mohammed, Arifuddin; Pujitha, Sravya; Sethi, Aaftaab; Supuran, Claudiu T. [Metabolites, 2020, vol. 10, # 4] Alvala, Mallika; Godugu, Chandraiah; Kalle, Arunasree M.; Kiranmai, Gaddam; Lakshmi Manasa, Kesari; Nagendra Babu, Bathini; Nagesh, Narayana; Sagar, Arpita; Sigalapalli, Dilep Kumar; Thatikonda, Sowjanya [Bioorganic Chemistry, 2020, vol. 101] He, Jun; Tang, Xue-Mei; Liu, Ting-Ting; Peng, Feng; Zhou, Qing; Liu, Li-Wei; He, Ming; Xue, Wei [Chemical Papers, 2021, vol. 75, # 3, p. 1021 - 1027]
[15]Bignon, Jérôme; El Abbouchi, Abdelmoula; El Brahmi, Nabil; El Kazzouli, Saïd; Guillaumet, Gérald; Hiebel, Marie-Aude; Suzenet, Franck [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 19]
[16]Wolff, Lisa; Bandaru, Siva Sankar Murthy; Eger, Elias; Lam, Hoai-Nhi; Napierkowski, Martin; Baecker, Daniel; Schulzke, Carola; Bednarski, Patrick J. [International Journal of Molecular Sciences, 2021, vol. 22, # 14]
  • 2
  • [ 27106-51-0 ]
  • [ 80852-47-7 ]
  • Naphthalene-2-sulfonic acid {1-(3-cyano-benzyl)-2-oxo-2-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide 1.) DMF, 1 h, 2.) DMF, RT, 20 h; Multistep reaction;
  • 3
  • [ 98-59-9 ]
  • 1-vinyloxycarbonylpiperazine [ No CAS ]
  • [ 27106-51-0 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 1-vinyloxycarbonylpiperazine With 2,2'-azobis(isobutyronitrile); Merrifield SH resin; reduced by dithiothreitol In N,N-dimethyl-formamide at 80℃; Stage #2: p-toluenesulfonyl chloride With pyridine Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid In dichloromethane
  • 4
  • 4-(toluene-4-sulfonyl)-piperazine-1-carboxylic acid 2-benzylsulfanyl-ethyl ester [ No CAS ]
  • [ 27106-51-0 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 4-(toluene-4-sulfonyl)-piperazine-1-carboxylic acid 2-benzylsulfanyl-ethyl ester With 3-chloro-benzenecarboperoxoic acid In dichloromethane Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;
  • 5
  • [ 27106-51-0 ]
  • 6-<i>tert</i>-butoxycarbonylamino-2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylamino)-3-(1<i>H</i>-indol-3-yl)-propionylamino]-hexanoic acid <i>tert</i>-butyl ester [ No CAS ]
  • 6-<i>tert</i>-butoxycarbonylamino-2-(3-(1<i>H</i>-indol-3-yl)-2-[4-(toluene-4-sulfonyl)-piperazine-1-carbonyl]-amino}-propionylamino)-hexanoic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran
  • 6
  • 4-(toluene-4-sulfonyl)-piperazine-1-carboxylic acid vinyl ester [ No CAS ]
  • [ 27106-51-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 87 percent / AIBN / dimethylformamide / 80 °C 2.1: mCPBA / CH2Cl2 2.2: 81 percent / DBU / CH2Cl2 / 2 h / 20 °C
  • 7
  • [ 27106-51-0 ]
  • 3-{2-(Naphthalene-2-sulfonylamino)-3-oxo-3-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-propyl}-benzamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) DMF, 1 h, 2.) DMF, RT, 20 h 2: H2S(g), TEA, pyridine / 48 h / Ambient temperature 3: dimethylformamide; acetone / 20 h / Ambient temperature 4: AcONH4 / methanol / 3 h / 60 °C
  • 8
  • [ 27106-51-0 ]
  • 3-{2-(Naphthalene-2-sulfonylamino)-3-oxo-3-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-propyl}-thiobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) DMF, 1 h, 2.) DMF, RT, 20 h 2: H2S(g), TEA, pyridine / 48 h / Ambient temperature
  • 9
  • [ 27106-51-0 ]
  • 3-{2-(Naphthalene-2-sulfonylamino)-3-oxo-3-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-propyl}-thiobenzimidic acid methyl ester; hydriodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) HOBt, DCC, 2.) N-methylmorpholine / 1.) DMF, 1 h, 2.) DMF, RT, 20 h 2: H2S(g), TEA, pyridine / 48 h / Ambient temperature 3: dimethylformamide; acetone / 20 h / Ambient temperature
  • 10
  • [ 27106-51-0 ]
  • 1,1-dimethylethyl 2-(4-(4-methylphenylsulfonyl)-1-piperazinyl)-2-oxo-1-(2-methylpropyl)ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.4% R.8 Reference Example 8 Reference Example 8 Using p-toluenesulfonylpiperazine in lieu of 1-(4-fluorophenyl)piperazine dihydrochloride, the procedure of Reference Example 5 was otherwise repeated to provide 1,1-dimethylethyl 2-(4-(4-methylphenylsulfonyl)-1-piperazinyl)-2-oxo-1-(2-methylpropyl)ethylcarbamate (6.95 g, 79.4%).
  • 11
  • [ 27106-51-0 ]
  • [ 107-04-0 ]
  • [ 53727-44-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene 3 Production of N-β-chloroethyl-N'-p-toluenesulfonylpiperazine: SPC13 After refluxing for 72 hours a reaction mixture consisting of 60 g (0.25 mol) of p-toluenesulfonylpiperazine (III), 41 ml (0.5 mol) of 1-bromo-2-chloroethane and 35 ml (0.25 mol) of triethylamine in 1 liter of benzene, the solution was filtered and white needle crystal were obtained from the filtrate. N-β-chloroethyl-N'-p-toluenesulfonylpiperazine 61 g (yield: 79%) was obtained.
  • 12
  • [ 27631-29-4 ]
  • [ 27106-51-0 ]
  • [ 1061767-97-2 ]
YieldReaction ConditionsOperation in experiment
67% In tetrahydrofuran
  • 13
  • 2-chloromethyl-3,5,6-trimethylpyrazine monohydrochloride [ No CAS ]
  • [ 27106-51-0 ]
  • [ 892495-38-4 ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine; sodium iodide In toluene for 10h; Reflux;
  • 15
  • [ 110-85-0 ]
  • [ 2232-08-8 ]
  • [ 27106-51-0 ]
Historical Records

Related Functional Groups of
[ 27106-51-0 ]

Sulfamides

Chemical Structure| 17046-84-3

[ 17046-84-3 ]

1,4-Ditosylpiperazine

Similarity: 1.00

Chemical Structure| 856843-84-0

[ 856843-84-0 ]

1-Tosylpiperazine hydrochloride

Similarity: 0.98

Chemical Structure| 100800-51-9

[ 100800-51-9 ]

1-Ethyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 46779-48-0

[ 46779-48-0 ]

1-Methyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 56187-04-3

[ 56187-04-3 ]

4-Methyl-N,N-bis(2-(4-methylphenylsulfonamido)ethyl)benzenesulfonamide

Similarity: 0.98

Aryls

Chemical Structure| 17046-84-3

[ 17046-84-3 ]

1,4-Ditosylpiperazine

Similarity: 1.00

Chemical Structure| 856843-84-0

[ 856843-84-0 ]

1-Tosylpiperazine hydrochloride

Similarity: 0.98

Chemical Structure| 100800-51-9

[ 100800-51-9 ]

1-Ethyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 46779-48-0

[ 46779-48-0 ]

1-Methyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 56187-04-3

[ 56187-04-3 ]

4-Methyl-N,N-bis(2-(4-methylphenylsulfonamido)ethyl)benzenesulfonamide

Similarity: 0.98

Related Parent Nucleus of
[ 27106-51-0 ]

Piperazines

Chemical Structure| 17046-84-3

[ 17046-84-3 ]

1,4-Ditosylpiperazine

Similarity: 1.00

Chemical Structure| 856843-84-0

[ 856843-84-0 ]

1-Tosylpiperazine hydrochloride

Similarity: 0.98

Chemical Structure| 100800-51-9

[ 100800-51-9 ]

1-Ethyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 46779-48-0

[ 46779-48-0 ]

1-Methyl-4-tosylpiperazine

Similarity: 0.98

Chemical Structure| 524711-31-7

[ 524711-31-7 ]

1-((3,4-Dimethylphenyl)sulfonyl)piperazine

Similarity: 0.95