2905-56-8|1-Benzylpiperidine| Ambeed

Abstract: Fentanyl (FTN) and synthetic analogs of FTN continue to ravage populations across the globe, including in the United States where opioids are increasingly being used and abused and are causing a staggering and growing number of overdose deaths each year. This growing pandemic is worsened by the ease with which FTN can be derivatized into numerous derivatives. Understanding the chemical properties/behaviors of the FTN class of compounds is critical for developing effective chemical detection schemes using nanoparticles (NPs) to optimize important chemical interactions. Halogen bonding (XB) is an intermolecular interaction between a polarized halogen atom on a molecule and e−-rich sites on another molecule, the latter of which is present at two or more sites on most fentanyl-type structures. Density functional theory (DFT) is used to identify these XB acceptor sites on different FTN derivatives. The high toxicity of these compounds necessitated a “fragmentation” strategy where smaller, non-toxic molecules resembling parts of the opioids acted as mimics of XB acceptor sites present on intact FTN and its derivatives. DFT of the fragments’ interactions informed solution measurements of XB using 19F NMR titrations as well as electrochemical measurements of XB at self-assembled monolayer (SAM)-modified electrodes featuring XB donor ligands. Gold NPs, known as monolayer-protected clusters (MPCs), were also functionalized with strong XB donor ligands and assembled into films, and their interactions with FTN “fragments” were studied using voltammetry. Ultimately, spectroscopy and TEM analysis were combined to study whole-molecule FTN interactions with the functionalized MPCs in solution. The results suggested that the strongest XB interaction site on FTN, while common to most of the drug’s derivatives, is not strong enough to induce NP-aggregation detection but may be better exploited in sensing schemes involving films.

Keywords: opioid ; fentanyl ; halogen bonding ; gold nanoparticle ; monolayer-protected cluster ; cyclic voltammetry

Purchased from AmBeed: 3489-28-9 ; 2905-56-8

Product Details of [ 2905-56-8 ]

CAS No. :	2905-56-8
Formula :	C₁₂H₁₇N
M.W :	175.27
SMILES Code :	C(N1CCCCC1)C1=CC=CC=C1
MDL No. :	MFCD00224901
InChI Key :	NZVZVGPYTICZBZ-UHFFFAOYSA-N
Pubchem ID :	76190

Safety of [ 2905-56-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 2905-56-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	60.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	3.24 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.59
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.14
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.67
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.94
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.59

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.77
Solubility	0.295 mg/ml ; 0.00168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.32
Solubility	0.844 mg/ml ; 0.00482 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.52
Solubility	0.0526 mg/ml ; 0.0003 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.52 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.0

Application In Synthesis of [ 2905-56-8 ]

* 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 [ 2905-56-8 ]

[ 2905-56-8 ] Synthesis Path-Downstream 1~55

1
[ 110-89-4 ]
[ 93-89-0 ]
[ 2905-56-8 ]

References: [1]Annali di Chimica,1957,vol. 47,p. 1177,1183.

2
[ 110-89-4 ]
[ 64-18-6 ]
[ 100-52-7 ]
[ 2905-56-8 ]

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Justus Liebigs Annalen der Chemie,1907,vol. 353,p. 292.
Chemisches Zentralblatt,1907,vol. 78,p. 53.

3
[ 110-89-4 ]
[ 107-31-3 ]
[ 100-52-7 ]
[ 2905-56-8 ]

References: [1]Patent: DE620510,1934,C .

4
[ 110-89-4 ]
[ 100-52-7 ]
[ 2905-56-8 ]

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5
[ 110-89-4 ]
[ 100-44-7 ]
[ 2905-56-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrabutylammomium bromide; sodium hydroxide; In water; at 100℃; for 1h;	General procedure: SiO2-CuI (0.1 g,5 mol% Cu) was added to a mixture of amine (0.5 mmol), benzyl chloride, allyl bromide, or n-butyl chloride (0.5 mmol for N-substitution and 1 mmol for N,N-disubstitution), NaOH (2 mmol), and TBAB (0.25 mmol) in a round-bottom flask(25 mL) in water (4mL). The reaction mixture was stirred at 15C (in the case of N-benzylation, allylation, or alkylation of primary amines,Table 2) or 70-100C (in the case of N,N-dibenzylation, allylation, or alkylation of primary amines, Table 3), and 100C(N-benzylation, allylation, and alkylation of secondary amines, Table 4) for an appropriate time. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was triturated with EtOAc (20 mL) and the SiO2-CuI was filtered off. The product was obtained after removal of the solvent under reduced pressure followed by column chromatography or crystallization from EtOAc-petroleum ether.
90%	With silica copper(I) oxide; tetrabutylammomium bromide; potassium carbonate; In water; at 100℃; for 0.5h;Green chemistry;	General procedure: A mixture of secondary amine (0.5 mmol), benzyl chloride (0.127 g, 1 mmol), K2CO3 (0.139 g, 1 mmol), TBAB (0.082 g,0.25 mmol), and SiO2-Cu2O (0.2 g, 5 mol% Cu) in water (5 mL) in a round-bottom flask (50 mL) was stirred at 100 C. On completionof the reaction (monitored by TLC), the flask was cooledto room temperature and the mixture filtered. The residue was washed with water followed by ethyl acetate (3 × 10 mL). The combined organic extracts were washed with water (3 × 100mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the product was obtainedby crystallization from petroleum ether or ethyl acetate/ petroleumether, or by eluting the crude product through a columnof silica gel with ethyl acetate/petroleum ether.
76%	With trimethylamine; In dichloromethane; at 20℃; for 6h;Inert atmosphere;	General procedure: Typical procedure: A solution of piperidine (0.84 g, 10.0 mmol), trimethylamine (1.01 g, 10.0 mmol) in dry CH2Cl2 (2 mL) under nitrogen atmosphere was cooled with an ice-water bath, then a solution of generation 1 bromide (3.83 g, 10.0 mmol) in dry CH2Cl2 (5mL) was slowly added. The mixture was stirred for 6 h at room temperature (TLC monitoring). After completion of the reaction, the crude product was puried by ash column chromatography on silica gel (petroleum ether: ethyl acetate 6:1,v/v) to afford 1-G1 as lightly yellow oil liquid.

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[9]Journal of Organic Chemistry,2011,vol. 76,p. 1425 - 1435.

6
[ 18811-61-5 ]
[ 60-29-7 ]
[ 591-51-5 ]
[ 2905-56-8 ]

References: [1]Chemische Berichte,1957,vol. 90,p. 8,14.

7
[ 776-75-0 ]
[ 2905-56-8 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 C for several hours to obtain the HCl salt of the amine.

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8
[ 94067-00-2 ]
phenylmagnesium bromide [ No CAS ]
[ 2905-56-8 ]

References: [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 839,841; engl. Ausg. S. 957.

9
[ 2937-99-7 ]
[ 2905-56-8 ]

References: [1]Bulletin de la Societe Chimique de France,1947,p. 454.
[2]Journal of Organic Chemistry,2008,vol. 73,p. 312 - 315.
[3]Catalysis science and technology,2014,vol. 4,p. 47 - 52.

10
[ 628-21-7 ]
[ 2905-56-8 ]
[ 121968-63-6 ]

References: [1],1956,vol. 5,p. 23,29,35.
Chem.Abstr.,1961,p. 5487.

11
[ 628-77-3 ]
[ 2905-56-8 ]
[ 121812-61-1 ]

References: [1],1956,vol. 5,p. 23,29,35.
Chem.Abstr.,1961,p. 5487.

12
[ 64-17-5 ]
[ 6633-92-7 ]
[ 2905-56-8 ]
[ 91061-28-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 884,892, 893.

13
[ 6633-92-7 ]
[ 2905-56-8 ]
[ 91061-28-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 884,892, 893.

14
[ 1600-27-7 ]
[ 64-19-7 ]
[ 2905-56-8 ]
[ 102666-89-7 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 5279,5286.

15
[ 96-32-2 ]
[ 2905-56-8 ]
[ 61533-06-0 ]

References: [1]Helvetica Chimica Acta,1931,vol. 14,p. 1007,1023.

16
[ 2905-56-8 ]
[ 106-95-6 ]
[ 22100-11-4 ]

References: [1]Chemische Berichte,1902,vol. 35,p. 182.

17
[ 2905-56-8 ]
[ 70-11-1 ]
1-benzyl-1-phenacyl-piperidinium; bromide [ No CAS ]

References: [1]Journal of the Chemical Society,1930,p. 2107,2112.

18
[ 2905-56-8 ]
[ 74-88-4 ]
[ 7596-28-3 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 19272 - 19280.
Angew. Chem.,2021,vol. 133,p. 19421 - 19429.
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[3]Journal of the Chemical Society,1903,vol. 83,p. 1144.

19
[ 2905-56-8 ]
[ 868-26-8 ]
[ 1733-15-9 ]

References: [1]Chemische Berichte,1901,vol. 34,p. 2073.
Justus Liebigs Annalen der Chemie,1911,vol. 378,p. 287.

20
[ 2905-56-8 ]
[ 29872-25-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dihydrogen peroxide; benzonitrile;Mg-Al-O-t-Bu HT (Catalyst B); In methanol; water; at 65℃; for 0.75h;Product distribution / selectivity;	Oxidation of various tertiary amines using catalyst B was carried out following the procedure as in example 2 and the results are given in Table 2.

References: [1]Patent: EP1348692,2003,A1 .Location in patent: Page/Page column 7.
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[9]Journal of Organic Chemistry,2011,vol. 76,p. 7842 - 7848.

21
[ 2905-56-8 ]
[ 59507-46-9 ]

References: [1]Journal of the Chemical Society,1926,p. 1665.

22
[ 2905-56-8 ]
[ 102666-89-7 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 5279,5286.

23
[ 2905-56-8 ]
1-benzyl-piperidine-1-oxide ; 1-benzyl-piperidine-1-oxide-hydrogen peroxid-adduct [ No CAS ]

References: [1]Archiv der Pharmazie,1954,vol. 287,p. 326.

24
[ 111-29-5 ]
[ 100-46-9 ]
[ 2905-56-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Bis(p-nitrophenyl) phosphate; In toluene; at 100℃; for 36h;Sealed tube; Molecular sieve; Green chemistry;	General procedure: Amine 11 (399.3 mg, 2.0 mmol, 1.0 eq.), diol 14 (379.7 mg, 2.4 mmol, 1.0eq.), were added to a sealed tube, 5.0 mL of toluene was added and stirred. Then [Ir] catalyst 15 (79.7 mg, 0.1 mmol, 0.05eq.) and phosphoric acid 16 (68.1 mg, 0.2 mmol, 0.1eq.), 4 molecular sieve (500.1 mg) was added, heated at 100 C for 36h. The reaction mass was allowed to cool to rt, then washed with 5% NaHCO3 solution, water, evaporated under vacuum. The crude mass was purified by silica gel column chromatography, eluted with 5% ethyl acetate in n-hexane to give clopidogrel (4) as a yellow oil.

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[10]Journal of Organic Chemistry,1985,vol. 50,p. 1365 - 1370.
[11]Journal of the American Chemical Society,1936,vol. 58,p. 2493.
[12]Analytical Chemistry,2014,vol. 86,p. 4024 - 4032.

25
[ 628-76-2 ]
[ 100-46-9 ]
[ 2905-56-8 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 2920.
[2]Chemische Berichte,1904,vol. 37,p. 2920.
[3]Patent: DE164365,1904,C .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.

26
[ 110-89-4 ]
[ 908094-04-2 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 4759 - 4762.
[2]Israel Journal of Chemistry,1991,vol. 31,p. 215 - 222.

27
[ 110-89-4 ]
[ 47484-87-7 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

28
[ 110-89-4 ]
[ 66310-10-9 ]
[ 580-35-8 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2697 - 2699.
[2]Journal of the Chemical Society. Perkin transactions II,1987,p. 73 - 78.
[3]Journal of Chemical Research, Miniprint,1983,p. 301 - 320.

29
[ 110-89-4 ]
[ 76017-39-5 ]
[ 67913-78-4 ]
[ 2905-56-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1987,p. 73 - 78.

30
[ 110-89-4 ]
[ 75505-88-3 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

31
[ 110-89-4 ]
[ 75505-89-4 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

32
[ 110-89-4 ]
[ 75505-95-2 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

33
[ 110-89-4 ]
[ 75505-90-7 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

34
[ 110-89-4 ]
[ 75505-92-9 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

35
[ 110-89-4 ]
[ 75505-91-8 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

36
[ 110-89-4 ]
[ 75505-93-0 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

37
[ 110-89-4 ]
[ 75505-94-1 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2701 - 2703.

38
[ 110-89-4 ]
[ 86018-81-7 ]
[ 2905-56-8 ]
2-(2',5'-dichlorophenyl)-4,6-diphenylpyridine [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1983,p. 301 - 320.

39
[ 110-89-4 ]
[ 75864-90-3 ]
[ 67913-78-4 ]
[ 2905-56-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1987,p. 73 - 78.

40
[ 110-89-4 ]
1-benzyl-5,6-dihydro-2,4-diphenylbenzo<h>quinolinium perchlorate [ No CAS ]
[ 67913-78-4 ]
[ 2905-56-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1987,p. 73 - 78.

41
[ 110-89-4 ]
1-Benzyl-6-methylthio-2,4-diphenyl-pyridinium-tetrafluoroborat [ No CAS ]
[ 113848-75-2 ]
[ 2905-56-8 ]

References: [1]Monatshefte fur Chemie,1987,vol. 118,p. 485 - 502.

42
[ 110-89-4 ]
[ 76016-88-1 ]
[ 580-35-8 ]
[ 2905-56-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1987,p. 73 - 78.

43
[ 110-89-4 ]
[ 103-67-3 ]
[ 2905-56-8 ]
[ 74-89-5 ]

References: [1]Journal of the American Chemical Society,1983,vol. 105,p. 5002 - 5011.

44
[ 110-89-4 ]
1-benzyl-2-(2',5'-dimethylphenyl)-4,6-diphenylpyridinium tetrafluoroborate [ No CAS ]
[ 2905-56-8 ]
2-(2',5'-dimethylphenyl)-4,6-diphenylpyridine [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1983,p. 301 - 320.

45
[ 110-89-4 ]
1-benzyl-2-(1-naphthyl)-4,6-diphenylpyridinium tetrafluoroborate [ No CAS ]
[ 3557-57-1 ]
[ 2905-56-8 ]

References: [1]Journal of Chemical Research, Miniprint,1983,p. 301 - 320.

46
[ 110-89-4 ]
[ 100-51-6 ]
[ 2905-56-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 145℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: Synthesis of tribenzylamine (4a): Under nitrogen atmosphere, to a 15-mL Pyrex glass screw-cap tube were added 1n (107 mg, 1 mmol), 2a (5 mL), and the Pt-Sn/γ-Al2O3 catalyst (98 mg, 0.25 mol % Pt). The resultant mixture was stirred in the sealed tube at 145 C for 8 h. After cooled to ambient temperature, the catalyst was removed by centrifugation and washed with Et2O (25 mL). The combined supernatant was concentrated under reduced pressure and then subjected to purification by silica gel column chromatography (eluent: petroleum ether (60-90 C)/EtOAc = 20:1, v/v), affording product 4a as a white solid (273 mg, 95%).
91%	In o-xylene; at 150℃; for 30h;Inert atmosphere; Sealed tube;	General procedure: Dried pressure tube was charged with magnetic stir bar and50 mg of PdSiO2 catalysts (1 mol% with respect to amine). Then,1.0 mL o-xylene was added, followed by the addition of 0.5 mmolof amine and 1 mmol of benzyl alcohol. The pressure tube wasflushed with argon was closed with screw cap. Then it was placedin the preheated aluminum block and reaction was allowed to progressfor 30 h at 150 C. After completion of the reaction, pressuretube was removed from aluminum block and cooled down to roomtemperature. The catalyst was filtered out by ciliate and reactionproducts were analyzed by GC-MS and the corresponding amineswere purified by column chromatography. The yields of selectedamines were determined by GC analysis using n-hexadecane asstandard. For this purpose, after completion of the reaction, nhexadecane(100 mL) as standard was added to the reaction pressuretube and the reaction products were diluted with ethyl acetate followed by filtration using plug of silica and then subjected GCanalysis.
79%	With trifuran-2-yl-phosphane; palladacycle; lithium hydroxide; In neat (no solvent); at 100℃; for 24h;Molecular sieve; Inert atmosphere;	General procedure: An oven dried Schlenk tube was charged with amine (3.0 mmol), alcohol (3.6 mmol), LiOH (1.5 mmol), palladacycle (6.010-3 mmol, 0.20 mol %), P(2-Fur)3 (12.010-3 mmol, 0.40 mol %) and activated 4 Å MS (100 mg) in argon atmosphere. The reaction mixture was stirred at 100 C for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and washed with water followed by brine solution. The organic phase was dried over anhydrous sodium sulphate. After removal of the solvent, the crude was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixtures to afford the N-alkylated product.

83%Chromat.

With CuO#NiO; at 145℃; for 18h;Inert atmosphere;

[0044] With reference to the conditions used in Examples 9-16, 60-150 mg of catalyst D obtained in Example 4 was weighted and added into a 40 mL glass reaction tube provided with a magnetic stirring apparatus containing 5 mmol amines having different structures and 5 mmol alcohols having different structures, respectively. After sealed, the tube was purged with N2 to replace the air in the system for three times. Next, the system was heated and stirred. The temperature was raised to 80-180 C. and then kept for 6-36 hours. The reaction was then stopped and the system was cooled down to the room temperature. The catalyst was obtained from the reaction mixture by filtration. Agilent 7890A (30 m×0.25 mm×0.33 μm capillary column, hydrogen flame ionization detector) gas chromatograph was used for quantitatively analyzing the reaction mixture. The other byproducts were qualitatively analyzed with Agilent 6890/5973 Gas Chromatography-Mass Spectrometer (equipped with NIST Mass Spectral Database chemical workstation, 30 m×0.25 mm×0.33 μm capillary column). Each of the analysis results was shown in Table 2.

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[26]Journal of the Chemical Society. Perkin transactions I,1984,p. 2415 - 2420.
[27]Journal of the Chemical Society. Chemical communications,1983,p. 682 - 684.
[28]Organic Letters,2011,vol. 13,p. 5386 - 5389.
[29]Organic and Biomolecular Chemistry,2022,vol. 20,p. 831 - 839.
[30]Chemical Communications,2011,vol. 47,p. 6981 - 6983.
[31]European Journal of Inorganic Chemistry,2011,p. 4801 - 4806.
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[33]Patent: US2014/39181,2014,A1 .Location in patent: Paragraph 0044.
[34]Applied Organometallic Chemistry,2017,vol. 31.
[35]European Journal of Organic Chemistry,2019,vol. 2019,p. 3105 - 3111.

47
[ 17206-00-7 ]
phenylmagnesium bromide [ No CAS ]
[ 2905-56-8 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 735 - 740.

48
[ 109-96-6 ]
[ 109-97-7 ]
[ 98-88-4 ]
[ 6913-92-4 ]
[ 2905-56-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2023 - 2026.

49
[ 4783-65-7 ]
[ 2905-56-8 ]

References: [1]Synthesis,1980,p. 695 - 697.
[2]Angewandte Chemie - International Edition,2009,vol. 48,p. 9507 - 9510.
[3]Synlett,2010,p. 1829 - 1832.
[4]ChemCatChem,2017,vol. 9,p. 2009 - 2017.
[5]Tetrahedron Letters,1980,vol. 21,p. 4061 - 4064.
[6]Journal of the American Chemical Society,2012,vol. 134,p. 640 - 653.

50
[ 29872-25-1 ]
[ 2905-56-8 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 7842 - 7848.
[2]Chemistry Letters,1985,p. 1517 - 1520.
[3]Chemical Communications,2015,vol. 51,p. 7035 - 7038.

51
[ 17642-89-6 ]
[ 2905-56-8 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 4061 - 4064.

52
[ 93-89-0 ]
sodium diethylpiperidinohydroaluminate [ No CAS ]
[ 2905-56-8 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 1941 - 1944.

53
[ 126216-53-3 ]
[ 2905-56-8 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 3205 - 3209.
[2]Tetrahedron,1991,vol. 47,p. 2683 - 2732.

54
[ 61135-82-8 ]
[ 2905-56-8 ]

References: [1]Journal of Organic Chemistry,1981,vol. 46,p. 3730 - 3732.

55
[ 2538-76-3 ]
[ 110-89-4 ]
[ 2905-56-8 ]

References: [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2868 - 2873.

Historical Records

Technical Information

• Reactions of Benzene and Substituted Benzenes

Related Functional Groups of
[ 2905-56-8 ]

Aryls

A383339 [29897-82-3]

1-Benzylpyrrolidine

Similarity: 0.91

A487638 [102-05-6]

N-Benzyl-N-methyl-1-phenylmethanamine

Similarity: 0.90

A199210 [1205-72-7]

1-Benzylpiperidin-4-amine dihydrochloride

Similarity: 0.89

A278850 [40240-12-8]

1-Benzyl-1,2,3,6-tetrahydropyridine

Similarity: 0.88

A495353 [6913-92-4]

1-Benzyl-3-pyrroline

Similarity: 0.88

Related Parent Nucleus of
[ 2905-56-8 ]

Piperidines

A199210 [1205-72-7]

1-Benzylpiperidin-4-amine dihydrochloride

Similarity: 0.89

A129898 [60407-35-4]

1-Benzylpiperidin-3-amine

Similarity: 0.86

A150486 [29608-05-7]

4-(Piperidin-1-ylmethyl)aniline

Similarity: 0.86

A200174 [368429-78-1]

1-Benzylpiperidin-3-amine hydrochloride

Similarity: 0.84

A612978 [4727-72-4]

1-Benzylpiperidin-4-ol

Similarity: 0.84

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
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H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 2905-56-8 ]

Aryls

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Aryls

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Piperidines

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