[ CAS No. 23936-11-0 ] {[proInfo.proName]}

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Quality Control of [ 23936-11-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 23936-11-0 ]

Product Details of [ 23936-11-0 ]

CAS No. :	23936-11-0	MDL No. :	MFCD00154705
Formula :	C₅H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BSPUWRUTIOUGMZ-UHFFFAOYSA-N
M.W :	114.15	Pubchem ID :	5106600
Synonyms :

Safety of [ 23936-11-0 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P261-P264-P280-P285-P304+P341-P305+P351+P338-P337+P313-P342+P311-P501	UN#:	N/A
Hazard Statements:	H303-H319-H334	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23936-11-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 23936-11-0 ]
Downstream synthetic route of [ 23936-11-0 ]

[ 23936-11-0 ] Synthesis Path-Upstream 1~2

1
[ 23936-11-0 ]
[ 25057-77-6 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 752 - 756

2
[ 23936-11-0 ]
[ 24424-99-5 ]
[ 76003-30-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 16 h;	Di-tert-butyl dicarbonate (1.99 g, 9.12 mmol) was added at room temperature to a solution of 3-methyl-2-oxopiperazine (1.04 g, 9.12 mmol) in dichloromethane (10 ml). After 16 h the reaction mixture was poured onto water. The organic layer was washed with brine, dried (MgSO₄), and concentrated to produce the title compound (2.12 g, 100percent). White solid, MS (ISP) 215.3 (M+H)⁺.
99%	With sodium carbonate In tetrahydrofuran; water for 4 h;	To 3-methylpiperazin-2-one (1.08 g, 9.33 mmol) in 1 : 1 THF/H₂O (45 mL) was added Na₂CO₃ (2.08 g, 19.60 mmol) and BOC-anhydride (2.24 g, 10.27 mmol). The reaction was allowed to stir for 4h, then extracted with DCM. The combined organics were washed lx with brine, dried over Na₂S0₄, filtered and concentrated in vacuo (2.00 g, 99percent).
72%	Stage #1: With triethylamine In dichloromethane at 20℃; for 0.166667 h; Inert atmosphere Stage #2: at 0 - 20℃; for 1 h;	Step 1: Synthesis of ie/t-butyl 2-methyl-3-oxopiperazine-l-carboxylate 1.2bNEt₃ (20 mL, 145 mmol) was added to a solution of 3-methylpiperazin-2-one 1.1b (15 g, 131 mmol) in anhydrous DCM (200 mL) under N₂ at RT. After 10 min stirring, the reaction mixture was cooled to 0°C and Boc₂0 (33 g, 151 mmol). The reaction mixture was stirred at RT for lh and thereupon washed with 0.5M HC1 (150 mL), brine (150 mL), dried over MgS0₄, filtered and concentrated to constant weight furnishing 2.2 as yellow oil (20.2 g, 72 percent). LCMS: P = 100 , retention time = 2.0 min, (M+H-iBu)⁺: 159

Reference： [1] Patent: US2009/23713, 2009, A1, . Location in patent: Page/Page column 16
[2] Patent: JP2017/527588, 2017, A, . Location in patent: Paragraph 0232
[3] Patent: WO2013/50424, 2013, A1, . Location in patent: Page/Page column 108-109
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3157 - 3163

[ 23936-11-0 ] Synthesis Path-Downstream 1~7

1
[ 23936-11-0 ]
[ 25057-77-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 752 - 756

2
[ 23936-11-0 ]
[ 24424-99-5 ]
[ 76003-30-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane; at 20℃; for 16h;	Di-tert-butyl dicarbonate (1.99 g, 9.12 mmol) was added at room temperature to a solution of 3-methyl-2-oxopiperazine (1.04 g, 9.12 mmol) in dichloromethane (10 ml). After 16 h the reaction mixture was poured onto water. The organic layer was washed with brine, dried (MgSO4), and concentrated to produce the title compound (2.12 g, 100%). White solid, MS (ISP) 215.3 (M+H)+.
99%	With sodium carbonate; In tetrahydrofuran; water; for 4h;	To 3-methylpiperazin-2-one (1.08 g, 9.33 mmol) in 1 : 1 THF/H2O (45 mL) was added Na2CO3 (2.08 g, 19.60 mmol) and BOC-anhydride (2.24 g, 10.27 mmol). The reaction was allowed to stir for 4h, then extracted with DCM. The combined organics were washed lx with brine, dried over Na2S04, filtered and concentrated in vacuo (2.00 g, 99%).
72%		Step 1: Synthesis of ie/t-butyl 2-methyl-3-oxopiperazine-l-carboxylate 1.2bNEt3 (20 mL, 145 mmol) was added to a solution of 3-methylpiperazin-2-one 1.1b (15 g, 131 mmol) in anhydrous DCM (200 mL) under N2 at RT. After 10 min stirring, the reaction mixture was cooled to 0C and Boc20 (33 g, 151 mmol). The reaction mixture was stirred at RT for lh and thereupon washed with 0.5M HC1 (150 mL), brine (150 mL), dried over MgS04, filtered and concentrated to constant weight furnishing 2.2 as yellow oil (20.2 g, 72 %). LCMS: P = 100 , retention time = 2.0 min, (M+H-iBu)+: 159

Reference： [1]Patent: US2009/23713,2009,A1 .Location in patent: Page/Page column 16
[2]Patent: JP2017/527588,2017,A .Location in patent: Paragraph 0232
[3]Patent: WO2013/50424,2013,A1 .Location in patent: Page/Page column 108-109
[4]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3157 - 3163

3
[ 23936-11-0 ]
[ 7312-27-8 ]
[ 1101840-32-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 4-methyl-morpholine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	A solution of 3,4-dichlorocinnamic acid (190 mg, 0.88 mmol), 3-methylpiperazin-2-one (100 mg, 0.88 mmol), 4-methylmorpholine (443 mg, 4.38 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoro-phosphate (500 mg, 1.31 mmol) in N,N-dimethylformamide (1 ml) was stirred at room temperature for 3 h, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH 95:5) produced the title compound (192 mg, 70%). White solid, MS (ISP)=313.1 (M+H)+.

Reference： [1]Patent: US2009/23713,2009,A1 .Location in patent: Page/Page column 15

4
[ 23936-11-0 ]
[ 393-09-9 ]
[ 1206601-10-6 ]

Yield	Reaction Conditions	Operation in experiment
24%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 140℃; for 0.166667h;Microwave irradiation;	A) 3-Methyl-4-(4-nitro-3-trifluoromethyl-phenyl)-piperazin-2-one; A mixture of 3-methyl-2-ketopiperazine (200 mg, 1.75 mmol), 5-fluoro-2-nitrobenzo-trifluoride (366 mg, 1.75 mmol), N,N-diisopropylethylamine and N,N-dimethylformamide (1 mL) was heated at 140 C. for 10 min under microwave irradiation, then partitioned between sat. aq. ammonium chloride solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 4:1) produced the title compound (130 mg, 24%). Yellow solid, MS: 304.1 (M+H)+.

Reference： [1]Patent: US2010/22518,2010,A1 .Location in patent: Page/Page column 49

5
[ 23936-11-0 ]
C₁₅H₂₀O₂ [ No CAS ]
[ 922178-61-8 ]
[ 78551-38-9 ]
[ 1394957-77-7 ]
(3R)-4-(3-mesitylpropanoyl)-3-methylpipera-zin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80 % ee 2: 58 % ee	With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; potassium carbonate In Isopropyl acetate at 23℃; for 24h; Resolution of racemate;

Reference： [1]Hsieh, Sheng-Ying; Binanzer, Michael; Kreituss, Imants; Bode, Jeffrey W. [Chemical Communications, 2012, vol. 48, # 71, p. 8892 - 8894]

6
[ 23936-11-0 ]
[ 1346681-71-7 ]
[ 922178-61-8 ]
[ 78551-38-9 ]
[ 1394957-77-7 ]
(3R)-4-(3-mesitylpropanoyl)-3-methylpipera-zin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 42% 2: 56%	With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; potassium carbonate In Isopropyl acetate at 23℃; for 24h;	20 Example 20: Kinetic Resolution of Racemic 3-methylpiperazin-2-one General procedure: Example 19: Improved General Procedure for the KineticResolution of Secondary AminesThe hydroxamic acid co-catalyst of example 18 (7.1 mg, 25 pmol, 0.05 equiv) , triazolium salt (16.4 mg, 50 μιηο, 0.10 equiv), ' -hydroxyenone (81.4 mg, 0.35 mmol, 0.70 equiv), K2C03 (13.8 mg, 0.1 mmol, 0.20 equiv) and the respective amine (0.50 mmol, 1.00 equiv) were dissolved in iPrOAc (2.5 ml, 0.20 M) and the reaction mixture was stirred at 23 °C for 24 hours.EtOAc (25 ml) was added, the mixture was filtered through Celite and concentrated in vacuo. The crude products were purified by column chromatography. Example 20: Kinetic Resolution of Racemic 3-Methylpip zin-2-oneRacemic 3-methylpiperazin-2-one (57.1 mg, 0.50 mmol) was resolved according to the improved general procedure (Example 19) .Recovered amine: 24 mg (42%, er = 90:10); acylated product: 80 mg (56%, er = 79:21).Calculated conversion: 58%; s = 9.Recovered amine: (3R) -3-methylpiperazin-2-oneThe amine was protected with benzyl chloroformate to determine the er:[a] 28D (c = 0.2, CHC13) : +/- 0.0;SFC : column: Daicel Chiralpak ASH (4.6 χ 250 mm) ; gradient: 5% iPrOH in C02 to 50% iPrOH in C02 over 10 min; flow: 3.0 ml/min; detection: 254 nm. Retention time: tR = 6.8 min (major) and 7.3 min (minor) .Amide product: (3S) -4- (3-Mesitylpropanoyl) -3-methylpipera- zin-2-one Me O Me [a] D (c = 4.0, CHC13) : +59.6; at room temperature the ratio of rotamers was 50:50 as determined by XH NMR;13C NMR (100 MHz, CDC13) : δ [ppm] = 171.9, 170.8, 170.5, 170.3, 136.0, 135.9, 135.7, 134.2, 134.1, 129.0, 53.9, 51.2, 41.3, 41.2, 38.9, 34.4, 32.4, 31.8, 24.7, 24.6, 20.7, 19.7, 17.8, 16.4;XH NMR (400 MHz, CDCI3) : δ [ppm] = 6.83 (s, 2 H) , 5.05 (q, J = 7.1 Hz, 0.5 H), 4.70 (dd, J = 13.6, 2.4 Hz, 0.5 H) , 4.28 (q, J = 7.1 Hz, 0.5 H), 3.69 (br d, J = 12.6 Hz, 0.5 H) , 3.46-3.21 (m, 2.5 H) , 3.05-2.90 (m, 2.5 H) , 2.58-2.32 (m, 2 H), 2.28 (s, 6 H) , 2.23 (s, 3 H) ; 1.44 (t, J = 6.5 Hz, 3 H) ;HRMS (ESI): calculated for [C17H25N2O2] + : m/z = 289.1911, found: m/z = 289.1914;IR (v /cm-1, neat) : 3244, 2998, 2944, 2921, 1668, 1648, 1457, 1427, 1332, 1208, 1091, 1062;SFC: column: Daicel Chiralpak ODH (4.6 * 250 mm); gradient: 5% iPrOH in C02 to 50% iPrOH in C02 over 10 min; flow: 3.0 ml/min; detection: 254 nm. Retention time: tR = 7.8 min (minor) and 9.4 min (major).

Reference： [1]Current Patent Assignee: EIDGENÖSSISCHE TECHNISCHE HOCHSCHULE ZÜRICH - WO2013/7371, 2013, A2 Location in patent: Page/Page column 69; 70; 71

7
[ 19838-07-4 ]
[ 23936-11-0 ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 6486 - 6493

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[ CAS No. 23936-11-0 ] {[proInfo.proName]}

Quality Control of [ 23936-11-0 ]

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Safety of [ 23936-11-0 ]

Application In Synthesis of [ 23936-11-0 ]

[ 23936-11-0 ] Synthesis Path-Upstream 1~2

[ 23936-11-0 ] Synthesis Path-Downstream 1~7

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