2905-56-8|1-Benzylpiperidine| Ambeed

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Quality Control of [ 2905-56-8 ] Purity: 98% SDS Specification

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Functionalized Gold Nanoparticles and Halogen Bonding Interactions Involving Fentanyl and Fentanyl Derivatives

Molly M. Sherard ; Jamie S. Kaplan ; Jeffrey H. Simpson ; Kevin W. Kittredge ; Michael C. Leopold ;

DOI: 10.3390/nano14110917 Nanomaterials,2024,14(11):917.

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 1~35

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 ]

References: [1]Justus Liebigs Annalen der Chemie,1905,vol. 343,p. 52.
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 ]

References: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1927 - 1930.
[2]Synthetic Communications,2010,vol. 40,p. 951 - 956.
[3]Journal of the Iranian Chemical Society,2010,vol. 7,p. 428 - 431.
[4]Turkish Journal of Chemistry,2010,vol. 34,p. 307 - 312.
[5]Chinese Chemical Letters,2010,vol. 21,p. 47 - 50.
[6]Synthesis,2011,p. 490 - 496.
[7]Synthetic Communications,2009,vol. 39,p. 2907 - 2916.
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[14]Tetrahedron Letters,2010,vol. 51,p. 3167 - 3169.
[15]Synlett,2006,p. 431 - 434.
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    Angew. Chem.,2017,vol. 129,p. 9640 - 9644,5.
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[25]RSC Advances,2015,vol. 5,p. 2292 - 2298.
[26]Tetrahedron,2008,vol. 64,p. 1213 - 1217.
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    Justus Liebigs Annalen der Chemie,1907,vol. 353,p. 292.
    Chemisches Zentralblatt,1907,vol. 78,p. 53.
[28]Journal of Organic Chemistry,1949,vol. 14,p. 559,572.
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    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 22,p. 183.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 22,p. 183.
[35]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4699 - 4704.
[36]Organic Process Research and Development,2020,vol. 24,p. 1647 - 1657.

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.

References: [1]Synthetic Communications,2014,vol. 44,p. 620 - 632.
[2]Helvetica Chimica Acta,2001,vol. 84,p. 3357 - 3365.
[3]Cuihua Xuebao/Chinese Journal of Catalysis,2014,vol. 35,p. 444 - 450.
[4]Green Chemistry,2009,vol. 11,p. 1115 - 1120.
[5]Green Chemistry,2013,vol. 15,p. 970 - 975.
[6]Tetrahedron Letters,2016,vol. 57,p. 2320 - 2323.
[7]Chemische Berichte,1882,vol. 15,p. 425.
[8]Journal of Organic Chemistry,2003,vol. 68,p. 613 - 616.
[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.

References: [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9507 - 9510.
[2]Organic Letters,2015,vol. 17,p. 446 - 449.
[3]Journal of Organic Chemistry,2014,vol. 79,p. 7728 - 7733.
[4]Chemical Communications,2018,vol. 54,p. 5855 - 5858.
[5]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3358 - 3362.
[6]Bulletin of the Polish Academy of Sciences: Chemistry,1986,vol. 34,p. 205 - 218.
[7]Chemical Communications,2013,vol. 49,p. 9758 - 9760.
[8]Advanced Synthesis and Catalysis,2016,vol. 358,p. 452 - 458.
[9]Organometallics,2013,vol. 32,p. 7440 - 7444.
[10]Chemical Communications,2021,vol. 57,p. 9204 - 9207.
[11]European Journal of Organic Chemistry,2013,p. 2066 - 2070.
[12]Journal of the American Chemical Society,2008,vol. 130,p. 18 - 19.
[13]Journal of Organic Chemistry,2021,vol. 86,p. 15992 - 16000.
[14]Tetrahedron,1998,vol. 54,p. 10899 - 10914.
[15]Journal of the American Chemical Society,2010,vol. 132,p. 1770 - 1771.
[16]Chemistry - A European Journal,2011,vol. 17,p. 1768 - 1772.
[17]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4817 - 4824.
[18]Cuihua Xuebao/Chinese Journal of Catalysis,2021,vol. 42,p. 2059 - 2067.
[19]ChemCatChem,2017,vol. 9,p. 2009 - 2017.
[20]Chemistry - A European Journal,2011,vol. 17,p. 12186 - 12192.
[21]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2775 - 2780.
[22]ChemCatChem,2019,vol. 11,p. 3818 - 3827.
[23]Tetrahedron Letters,2008,vol. 49,p. 6873 - 6875.
[24]European Journal of Organic Chemistry,2014,vol. 2014,p. 5144 - 5148.
[25]Chemische Berichte,1899,vol. 32,p. 74.
[26]Archiv der Pharmazie,1927,p. 390,400.
    Chemisches Zentralblatt,1924,vol. 95,p. 1404.
[27]Journal of Organic Chemistry,1953,vol. 18,p. 1190,1196.
[28]Journal of Organic Chemistry,1981,vol. 46,p. 3730 - 3732.
[29]Journal of the American Chemical Society,2008,vol. 130,p. 933 - 944.
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    Angew. Chem.,2017,vol. 129,p. 16117 - 16120,4.
[35]Patent: DE164365,1904,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
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    Angew. Chem.,2021,vol. 133,p. 16171 - 16179.

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.
[2]Bulletin des Societes Chimiques Belges,1959,vol. 68,p. 65,77.
[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.
[2]Chemical Communications,2001,p. 1736 - 1737.
[3]Archiv der Pharmazie,1954,vol. 287,p. 326.
[4]Chemische Berichte,1899,vol. 32,p. 2518.
[5]Chemische Berichte,1958,vol. 91,p. 67,75.
[6]Synthesis,1985,p. 770 - 773.
[7]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 3291 - 3298.
[8]Tetrahedron,1997,vol. 53,p. 15877 - 15888.
[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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25
[ 628-76-2 ]
[ 100-46-9 ]
[ 2905-56-8 ]

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[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 ]

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[2]Israel Journal of Chemistry,1991,vol. 31,p. 215 - 222.

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

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

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[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.

Historical Records

Technical Information

• Reactions of Benzene and Substituted Benzenes

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[ 2905-56-8 ]

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CAS No.: 2905-56-8

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