[ CAS No. 886766-60-5 ] {[proInfo.proName]}

Name: 886766-60-5|tert-Butyl 2-phenylpiperazine-1-carboxylate|98%
Brand: Ambeed
SKU: A548965
Price: 57.0 USD
Availability: InStock
Rating: 90 (25 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 886766-60-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 886766-60-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 886766-60-5 ]

SDS Specification

Alternatived Products of [ 886766-60-5 ]

Product Details of [ 886766-60-5 ]

CAS No. :	886766-60-5	MDL No. :	MFCD07367734
Formula :	C₁₅H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DVOURBIBCQYVCC-UHFFFAOYSA-N
M.W :	262.35	Pubchem ID :	16740572
Synonyms :

Safety of [ 886766-60-5 ]

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

Application In Synthesis of [ 886766-60-5 ]

* 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.

Downstream synthetic route of [ 886766-60-5 ]

[ 886766-60-5 ] Synthesis Path-Downstream 1~29

1
[ 886766-60-5 ]
[ 13790-39-1 ]
[ 1239955-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl acetamide at 100℃; for 3h;	4.1 Step 1. 4-Chloro-6,7-dimethoxyquinazoline (856 mg, 3.81 mmol), tert-butyl 2-phenylpiperazine-1-carboxylate (1.0 g, 3.81 mmol), N,N-dimethylacetamide (15 mL), tetra-n-butylammonium iodide (140 mg, 0.38 mmol) and potassium carbonate (1.58 g, 11.4 mmol) were combined and warmed to 100° C. for 3 hours, concentrated under vacuum at 55° C. and the residue was dissolved in 100 mL of water and 200 mL of DCM. The organic phase was separated, dried (MgSO4), concentrated and purified by column chromatography over silica gel using a gradient elution going from 0% MeOH to 5% MeOH in 1:1 EtOAc/hexane with 0.3% DMEA to provide tert-butyl 4-(6,7-dimethoxyquinazolin-4-yl)-2-phenylpiperazine-1-carboxylate as a white solid.

Reference： [1]Current Patent Assignee: AMGEN INC - US2007/265258, 2007, A1 Location in patent: Page/Page column 25

2
[ 886766-60-5 ]
2-chloro-7-(trifluoromethyl)-1H-benzimidazole [ No CAS ]
2-(3-phenyl-piperazin-1-yl)-4-trifluoromethyl-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-phenyl-piperazine-1-carboxylic acid tert-butyl ester; 2-chloro-7-(trifluoromethyl)-1H-benzimidazole With N-ethyl-N,N-diisopropylamine In acetonitrile at 90 - 170℃; for 2h; Microwave irradiation; Stage #2: With trifluoroacetic acid In dichloromethane at 50℃;	141 Example 141 Racemic Mixture Example 141 Racemic Mixture 2-Chloro-7-(Trifluoromethyl)-1H-Benzimidazole (220 mg, 1.0 mmol), 2-Phenyl-piperazine-1-carboxylic acid tert-butyl ester (400 mg, 1.5 mmol), N,N-diisopropylethylamine (500 μl, 2.9 mmol) are dissolved in 3 ml of acetonitrile and heated in a microwave reactor 1.5 hours at 160° C. and then 30 minutes at 170° C. The reaction mixture is stirred into an open flask at 90° C. to evaporate the solvent then the residue is dissolved in 4 ml of DCM; trifluoroacetic acid (2.0 ml, 26.0 mmol) is added and the reaction mixture is stirred until complete deprotection occurs; it is then concentrated at 50° C. The residue is dissolved in MeOH, basified by addition of Triethylamine and purified by preparative HPLC-MS to obtain 255 mg (74% yield) of the intermediate 2-(3-Phenyl-piperazin-1-yl)-4-trifluoromethyl-1H-benzoimidazole.N,N-diisopropylethylamine (50 μl, 0.29 mmol) and HATU (40 mg, 0.11 mmol) are added into a solution of tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide (18 mg, 0.10 mmol) dissolved in 2 ml of DMF. After 10 minutes stirring, 2-(3-Phenyl-piperazin-1-yl)-4-trifluoromethyl-1H-benzoimidazole (35 mg, 0.10 mmol, prepared as described above) is added and the reaction mixture is stirred overnight, diluted with Methanol, water and trifluoroacetic acid and finally purified by preparative HPLC-MS to obtain the title compound (41 mg, 81% yield on the last step). [0911] HPLC-MS (Method 19): Rt=1.19 min [0912] MS: m/z=507 [M+H]+

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2015/105397, 2015, A1 Location in patent: Paragraph 0908; 0909; 0910; 0911; 0912

3
[ 886766-60-5 ]
[ 1075753-27-3 ]
C₂₃H₂₅F₃N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 160 - 170℃; for 2h;Microwave irradiation;	2-Chloro-7-(Trifluoromethyl)-lH-Benzimidazole (220 mg, 1.0 mmol), 2-Phenyl- piperazine-l-carboxylic acid tert-butyl ester (400 mg, 1.5 mmol), N,N- diisopropylethylamine (500 mu, 2.9 mmol) are dissolved in 3 ml of acetonitrile and heated in a microwave reactor 1.5 hours at 160C and then 30 minutes at 170C. The reaction mixture is stirred into an open flask at 90C to evaporate the solvent then the residue is dissolved in 4 ml of DCM; trifluoroacetic acid (2.0 ml, 26.0 mmol) is added and the reaction mixture is stirred until complete deprotection occurs; it is then concentrated at 50C. The residue is dissolved in MeOH, basified by addition of Triethylamine and purified by preparative HPLC-MS to obtain 255 mg (74% yield) of the intermediate 2-(3- Phenyl-piperazin- 1 -yl)-4-trifluoromethyl- 1 H-benzoimidazole. N,N-diisopropylethylamine (50 mu, 0.29 mmol) and HATU (40 mg, 0.11 mmol) are added into a solution of tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide (18 mg, 0.10 mmol) dissolved in 2 ml of DMF. After 10 minutes stirring, 2-(3-Phenyl-piperazin-l-yl)-4- trifluoromethyl-lH-benzoimidazole (35 mg, 0.10 mmol, prepared as described above) is added and the reaction mixture is stirred overnight, diluted with Methanol, water and trifluoroacetic acid and finally purified by preparative HPLC-MS to obtain the title compund (41 mg, 81% yield on the last step). HPLC-MS (Method 19): Rt = 1.19 min MS: m/z = 507 [M+H]+

Reference： [1]Patent: WO2015/55698,2015,A1 .Location in patent: Page/Page column 177; 178

4
[ 886766-60-5 ]
C₂₄H₂₅F₃N₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 160 - 170 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane; acetonitrile 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2015/55698, 2015, A1

5
[ 886766-60-5 ]
2-(3-phenyl-piperazin-1-yl)-4-trifluoromethyl-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 160 - 170 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane; acetonitrile

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2015/55698, 2015, A1

6
[ 886766-60-5 ]
[ 373384-18-0 ]
tert-butyl 4-(3-(methylsulfonyl)phenyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; copper(II) acetate monohydrate In dichloromethane at 40℃; Molecular sieve;

Reference： [1]Zheng, Yajun; Zhuang, Linghang; Fan, Kristi Yi; Tice, Colin M.; Zhao, Wei; Dong, Chengguo; Lotesta, Stephen D.; Leftheris, Katerina; Lindblom, Peter R.; Liu, Zhijie; Shimada, Jun; Noto, Paul B.; Meng, Shi; Hardy, Andrew; Howard, Lamont; Krosky, Paula; Guo, Joan; Lipinski, Kerri; Kandpal, Geeta; Bukhtiyarov, Yuri; Zhao, Yi; Lala, Deepak; Van Orden, Rebecca; Zhou, Jing; Chen, Guozhou; Wu, Zhongren; McKeever, Brian M.; McGeehan, Gerard M.; Gregg, Richard E.; Claremon, David A.; Singh, Suresh B. [Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3264 - 3271]

7
[ 886766-60-5 ]
2-(4-(3-(methylsulfonyl)phenyl)-2-phenylpiperazin-1-yl)-4-(trifluoromethyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(II) acetate monohydrate; oxygen / dichloromethane / 40 °C / Molecular sieve 2: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 0.5 h / 160 °C / Microwave irradiation

8
[ 886766-60-5 ]
2-(4-(3-(methylsulfonyl)phenyl)-2-phenylpiperazin-1-yl)-4-(trifluoromethyl)pyrimidine [ No CAS ]
2-(4-(3-(methylsulfonyl)phenyl)-2-phenylpiperazin-1-yl)-4-(trifluoromethyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: copper(II) acetate monohydrate; oxygen / dichloromethane / 40 °C / Molecular sieve 2: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 0.5 h / 160 °C / Microwave irradiation 4: Column: AD-H; Method Name: AD-H_3_40_2.5ml.met / Resolution of racemate

9
[ 886766-60-5 ]
C₂₇H₃₇BN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 20 h / 105 °C 2: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.67 h / 110 °C / Microwave irradiation

Reference： [1]Qin, Lan-Ying; Ruan, Zheming; Cherney, Robert J.; Dhar, T.G. Murali; Neels, James; Weigelt, Carolyn A.; Sack, John S.; Srivastava, Anurag S.; Cornelius, Lyndon A.M.; Tino, Joseph A.; Stefanski, Kevin; Gu, Xiaomei; Xie, Jenny; Susulic, Vojkan; Yang, Xiaoxia; Yarde-Chinn, Melissa; Skala, Stacey; Bosnius, Ruth; Goldstein, Christine; Davies, Paul; Ruepp, Stefan; Salter-Cid, Luisa; Bhide, Rajeev S.; Poss, Michael A. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 4, p. 855 - 861]

10
[ 886766-60-5 ]
C₃₅H₄₀N₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 20 h / 105 °C 2: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.67 h / 110 °C / Microwave irradiation 3: sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 90 °C

11
[ 886766-60-5 ]
[ 108-36-1 ]
C₂₁H₂₅BrN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 105℃; for 20h;

12
[ 24424-99-5 ]
[ 886766-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dichloromethane 2: sodium hydride / N,N-dimethyl-formamide 3: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4: palladium on activated charcoal; hydrogen / methanol

Reference： [1]Usui, Yoshihiro; Uehara, Fumiaki; Hiki, Shinsuke; Watanabe, Kazutoshi; Tanaka, Hiroshi; Shouda, Aya; Yokoshima, Satoshi; Aritomo, Keiichi; Adachi, Takashi; Fukunaga, Kenji; Sunada, Shinji; Nabeno, Mika; Saito, Ken-Ichi; Eguchi, Jun-ichi; Yamagami, Keiji; Asano, Shouichi; Tanaka, Shinji; Yuki, Satoshi; Yoshii, Narihiko; Fujimura, Masatake; Horikawa, Takashi [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732]

13
[ 5368-28-5 ]
[ 886766-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dichloromethane 2: sodium hydride / N,N-dimethyl-formamide 3: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4: palladium on activated charcoal; hydrogen / methanol

14
[ 911705-40-3 ]
[ 886766-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 3: palladium on activated charcoal; hydrogen / methanol

15
C₂₂H₂₆N₂O₃ [ No CAS ]
[ 886766-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 2: palladium on activated charcoal; hydrogen / methanol

16
[ 911705-58-3 ]
[ 886766-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; hydrogen In methanol

17
[ 886766-60-5 ]
tert-butyl 4-(5-aminopentyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 110 °C / Microwave irradiation 2: hydrazine / ethanol / 20 °C

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2018/271837, 2018, A1

18
[ 886766-60-5 ]
tert-butyl 2-phenyl-4-(5-(5-(thiophen-2-yl)isoxazole-3-carboxamido)pentyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 110 °C / Microwave irradiation 2: hydrazine / ethanol / 20 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 110 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2018/271837, 2018, A1

19
[ 886766-60-5 ]
N-(5-(3-phenylpiperazin-1-yl)pentyl)-5-(thiophen-2-yl)isoxazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 110 °C / Microwave irradiation 2: hydrazine / ethanol / 20 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 110 °C / Microwave irradiation 4: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2018/271837, 2018, A1

20
[ 886766-60-5 ]
[ 954-81-4 ]
tert-butyl 4-(5-(1,3-dioxoisoindolin-2-yl)pentyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.5%	With caesium carbonate; In N,N-dimethyl-formamide; at 110℃; for 0.416667h;Microwave irradiation;	Step 1: Preparation of tert-Butyl 4-(5-(1,3-dioxoisoindolin-2-yl)pentyl)-2-phenylpiperazine-1-carboxylate In a microwave vial, tert-butyl 2-phenylpiperazine-1-carboxylate (500 mg, 1.906 mmol, 1 eq), cesium carbonate (1863 mg, 5.72 mmol, 3 eq), and <strong>[954-81-4]2-(5-bromopentyl)isoindoline-1,3-dione</strong> (564 mg, 1.906 mmol, 1 eq) were dissolved in DMF (3 mL). The reaction was put in the microwave for 25 min at 110 C. The mixture was taken up in EtOAc and water extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated, and purified by silica gel chromatography to give the title compound (460 mg, 50.5% yield) as a colorless oil.

Reference： [1]Patent: US2018/271837,2018,A1 .Location in patent: Paragraph 0174

21
[ 886766-60-5 ]
[ 27064-94-4 ]
tert-butyl 4-(bis(4-fluorophenyl)methyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.2%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃;	INTERMEDIATE 111 (1216) tert-butyl 4-(bis(4-fluorophenyl)methyl)-2-phenylpiperazine-1-carboxylate To a solution of 4,4’-(chloromethylene)bis(fluorobenzene) (75 mg, 0.314 mmol) in acetonitrile (20 mL) at room temperature were added tert-butyl 2-phenylpiperazine-1- carboxylate (91 mg, 0.346 mmol) and DIPEA (0.165 mL, 0.943 mmol) The reaction mixture was heated to 80 °C overnight and concentrated under reduced pressure. The residue was dissolved in DCM, washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using 24 g flash column, eluting with 30 % EtOAc in petroleum ether. The fractions were concentrated under reduced pressure to yield the product tert- butyl 4-(bis(4-fluorophenyl)methyl)-2-phenylpiperazine-1-carboxylate (100 mg, 65.2 % yield); LCMS: m/z = 465.5 (M+H); rt 1.63 min. LCMS Method: M. phase A: 10 mM ammonium acetate:acetonitrile (95:5) Mobile phase B: 10 mM ammonium (1218) acetate:acetonitrile (5:95) Method: %B: 0 min-20:2min-100:2.3min-100 Flow: 0.7 mL/min Column: AQUITY UPLC BEH C18 (3.0 x 50 mm) 1.7 ^m

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/6018, 2020, A1 Location in patent: Page/Page column 303; 304

22
[ 886766-60-5 ]
[ 5672-83-3 ]
tert-butyl 4-((S)-4-(((benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 16h;	1.1 ferf-butyl 4-((S)-4-(((benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoyl)-2-phenylpiperazine-1-carboxylate (3) A mixture of (S)-4-(((benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid (1) (1 g, 3.389 mmol), ferf-butyl 2- phenylpiperazine-1 -carboxylate (2) (888 mg, 3.389 mmol), and pyridine (2 mL, 1 vol) in EtOAc (40 mL) at 0 °C was treated with T3P (4.31 mL, 50 wt% in EtOAc, 16.129 mmol). The resulting mixture was stirred at RT for 16 h. The progress of the reaction was monitored by TLC and LCMS. After 16 h, reaction mixture was quenched with 1 N HCI (20 mL) and added water (50 mL), extracted with ethyl acetate (2 x 50 mL), the combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by silica gel column by eluting with 50% ethyl acetate in pet ether to afford ferf-butyl 4-((S)-4-(((benzyloxy)carbonyl)amino)-5-methoxy-5- oxopentanoyl)-2-phenylpiperazine-1-carboxylate (3). TLC system: 50% Ethyl acetate in pet ether, l: 0.3 LCMS (ESI): m/z 540.40 (M+H) +

Reference： [1]Current Patent Assignee: COCRYSTAL PHARMA, INC. - WO2021/206876, 2021, A1 Location in patent: Paragraph 00179

23
[ 886766-60-5 ]
tert-butyl 4-((S)-4-amino-5-methoxy-5-oxopentanoyl)-2-phenylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 16 h / 0 - 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C