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[ CAS No. 2359-60-6 ] {[proInfo.proName]}

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Chemical Structure| 2359-60-6
Chemical Structure| 2359-60-6
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Product Details of [ 2359-60-6 ]

CAS No. :2359-60-6 MDL No. :MFCD00051688
Formula : C11H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :TVOSOIXYPHKEAR-UHFFFAOYSA-N
M.W : 176.26 Pubchem ID :413501
Synonyms :

Calculated chemistry of [ 2359-60-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.3
TPSA : 29.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.75
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 2.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.202 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (Ali) : -3.02
Solubility : 0.169 mg/ml ; 0.000956 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.306 mg/ml ; 0.00174 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 2.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 2359-60-6 ]

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

Application In Synthesis of [ 2359-60-6 ]

* 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 [ 2359-60-6 ]
  • Downstream synthetic route of [ 2359-60-6 ]

[ 2359-60-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 6574-15-8 ]
  • [ 2359-60-6 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 3 h; 4-Fluoronitrobenzene (323 mg, 2.3 mmol) was dissolved in DMSO (5 ml), potassium carbonate (475 mg, 3.5 mmol) and piperidine (460 μl, 4.6 mmol) were added, and the mixture was stirred at 90° C. for 9 hr.
Then, water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate.
The organic layer was washed twice with saturated aqueous NaCl.
The organic layer was dried over Na2CO3, the solvent was evaporated to give compound Y197 (yield; 472 mg, 100percent).
Compound Y197 was dissolved in ethyl acetate (20 ml), Pd/C (186 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr.
Then, the reaction solution was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (40:1)) to give compound Y222 (yield, quantitative, 394 mg).
Compound Y491 (mentioned later) (80 mg, 0.18 mmol) was dissolved in dichloromethane (2 ml), compound Y222 (100 mg, 0.58 mmol) was added, and the mixture was stirred at room temperature for 5 hr.
Then, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (35:1)) to give the title compound (yield; 68 mg, 64percent).
1H NMR (500 MHz, CDCl3) δ8.40 (s, 1H), 8.0 (d, 1H, J=8.0 Hz), 7.70 (d, 1H, J=8.5 Hz), 7.52 (dd, 1H, J=8.0, 7.5 Hz), 6.92 (dd, 2H, J=9.0, 3.5 Hz), 6.77 (dd, 2H, J=9.0, 6.5 Hz), 5.33 (t, 1H, J=6.0 Hz), 4.07 (bs, 2H), 3.11-3.09 (m, 4H), 2.79-2.64 (m, 4H), 1.69-1.53 (m, 10H), 1.43 (s, 9H), 1.09-1.01 (m, 2H)
13C NMR (125 MHz, CDCl3) δ154.9, 141.6, 140.8, 131.4, 130.9, 129.8, 125.8, 125.7, 79.7, 77.4, 48.7, 36.6, 29.6, 28.6, 25.7, 24.2
HRMS (FAB-) m/z: [M-H]- calcd for C28H39N4O6S2, 591.2311. found, 591.2324
99% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 0.59 mL (6 mmol) piperidine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 50:1, 30:1) to afford 902 mg (87percent) yellow solid. The solid was dissolved in methanol, 90 mg Pd-C (10percent) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentratedin vacuo. The crude product was purified by flash chromatography (PEEA = 5:1) to afford 4l’ 0.706 g 99percent.
96%
Stage #1: With ammonium chloride In tetrahydrofuran; water at 75℃; for 0.5 h;
Stage #2: With water; iron In tetrahydrofuran at 75℃;
Synthesis of 4-Piperidin-1-yl-phenylamine
Ammonium chloride (228 mg, 4.2 mmol) in water (4 mL) was added to a solution of 1-(4-nitro-phenyl)-piperidine (220 mg, 1.0 mmol) in THF (6 mL) and the resulting mixture was stirred at 75° C. for 30 minutes.
Iron powder (238 mg, 4.2 mmol) was then added portion wise and the mixture stirred for 5 hours at 75° C.
The reaction mixture was filtered over celite, the filtrate was basified with sodium bicarbonate solution and the product extracted with ethyl acetate.
The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 180 mg (96percent) of 4-Piperidin-1-yl-phenylamine. LCMS: 177.13 (M+1)+, 80.6percent, 1H NMR: (DMSO-d6): δ 6.67 (m, 2H), 6.47 (m, 2H), 4.51 (s, 2H), 2.57 (t, 4H), 1.6 (q, 4H), 1.49 (m, 2H)
80% With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 12 h; Reflux The second step: to install a magnetic stir, thermometer, condenser 500mL three-necked flask is addedThe first step in the reaction of 15.0g of 4-nitrophenyl piperidine powder, 2.0g of 10percent mass fraction of Pd / C,180mL of ethanol was added as a solvent, and stirred to obtain a uniform suspension. After heating to reflux, the suspensionWas slowly added dropwise 45.0g of mass fraction of 80percent hydrazine hydrate solution, stirring continued at reflux for 12h. The reaction was completeCompleted, the reaction solution was filtered hot to remove Pd / C, the filtrate was concentrated under reduced pressure to 1/4 of its original volume, under a nitrogen atmosphereCooling and crystallization, to obtain a gray 4-aminophenyl-piperidine 10.2 g of crystals, 80percent yield;
75% With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 10 h; Reflux In a 500mL round-bottom flask, 28.3g (0.14mol) of nitro compound 1, 0.2g of 10 wtpercent Pd/C, 20mL hydrazine monohydrate and 180mL of ethanol was stirred at a reflux temperature for 10h. The solution was filtered hot to remove Pd/C, and the filtrate was evaporated under reduced pressure to dryness. A deep purplish red liquid was obtained. The product (2) was used for the next step without further purification. The yield was 18.1g (75percent). IR (KBr): 3429, 3346cm−1 (−NH2 str.). 1H NMR (500MHz, DMSO-d6, δ, ppm): 6.66 (d, J=8.8Hz, 2H, He), 6.48 (d, J=8.8Hz, 2H, Hd), 4.49 (s, 2H, −NH2), 2.84 (t, J=5.4Hz, 4H, Hc), 1.59 (m, 4H, Hb), 1.45 (m, 2H, Ha). 13C NMR (125MHz, DMSO-d6, δ, ppm): 143.5 (C4), 141.9 (C7), 118.6 (C6), 114.7 (C5), 52.1 (C3), 25.8 (C2), 23.8 (C1)
384 mg With iron; ammonium chloride In methanol; water at 100℃; General procedure: The compound S1 (261 mg, 1.25 mmol), iron powder (210 mg, 4.76 mmol, 3 equiv.) and ammonium chloride (335 mg, 6.27 mmol, 5 equiv.) were dissolved in methanol : water (2 : 1, 15 mL). The reaction mixture was heated at 100 °C overnight, cooled to RT, filtered through celite and the solvent was reduced under vacuum. The condensed mixture was extracted with DCM, washed with brine, dried with sodium sulfate and all solvent was evaporated to furnish the condensed residue, which was purified by flash chromatography (elution system - EA/Hexane = 1 : 1 ) to obtain the title compound (245 mg, 1.43 mmol).

Reference: [1] Patent: US2013/45977, 2013, A1, . Location in patent: Paragraph 0211; 0212; 0213; 0214
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[3] Patent: US2009/239848, 2009, A1, . Location in patent: Page/Page column 25
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 4849 - 4859
[5] Patent: CN105503775, 2016, A, . Location in patent: Paragraph 0042
[6] Reactive and Functional Polymers, 2016, vol. 108, p. 54 - 62
[7] Journal of Chemistry, 2014, vol. 2014,
[8] Journal of the American Chemical Society, 1948, vol. 70, p. 2223,2228
[9] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1803 - 1806
[10] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227
[11] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2371 - 2387
[12] Patent: WO2005/9978, 2005, A1, . Location in patent: Page 99; 101
[13] Patent: WO2005/42518, 2005, A2, . Location in patent: Page/Page column 99; 101
[14] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2763 - 2768
[15] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 731 - 738
[16] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 593 - 619
[17] European Journal of Medicinal Chemistry, 2019, p. 690 - 709
  • 2
  • [ 110-89-4 ]
  • [ 106-47-8 ]
  • [ 2359-60-6 ]
YieldReaction ConditionsOperation in experiment
76% With water; sodium t-butanolate In toluene at 105℃; for 9 h; Schlenk technique General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA–Pd (0.05 g, 0.04 mmol, 1.5 molpercent), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 2, p. 219 - 222
  • 3
  • [ 110-89-4 ]
  • [ 106-40-1 ]
  • [ 2359-60-6 ]
YieldReaction ConditionsOperation in experiment
70% With water; sodium t-butanolate In toluene at 105℃; for 5 h; Schlenk technique General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA–Pd (0.05 g, 0.04 mmol, 1.5 molpercent), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 2, p. 219 - 222
  • 4
  • [ 350-46-9 ]
  • [ 2359-60-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2371 - 2387
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1803 - 1806
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 731 - 738
[5] Journal of Chemistry, 2014, vol. 2014,
[6] Patent: CN105503775, 2016, A,
[7] Patent: US2013/45977, 2013, A1,
[8] European Journal of Medicinal Chemistry, 2019, p. 690 - 709
  • 5
  • [ 110-89-4 ]
  • [ 2359-60-6 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 458
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 731 - 738
[3] Journal of Chemistry, 2014, vol. 2014,
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[5] Patent: CN105503775, 2016, A,
[6] Reactive and Functional Polymers, 2016, vol. 108, p. 54 - 62
[7] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 593 - 619
[8] Patent: US2013/45977, 2013, A1,
[9] European Journal of Medicinal Chemistry, 2019, p. 690 - 709
  • 6
  • [ 1207-69-8 ]
  • [ 6574-15-8 ]
  • [ 2359-60-6 ]
Reference: [1] Patent: US2001/46991, 2001, A1,
  • 7
  • [ 110-89-4 ]
  • [ 106-39-8 ]
  • [ 2359-60-6 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 8, p. 2301 - 2305
  • 8
  • [ 586-78-7 ]
  • [ 2359-60-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
  • 9
  • [ 100-00-5 ]
  • [ 2359-60-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 593 - 619
  • 10
  • [ 4096-20-2 ]
  • [ 2359-60-6 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 458
  • 11
  • [ 61083-49-6 ]
  • [ 2359-60-6 ]
Reference: [1] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1565,1567; engl. Ausg. S. 1638, 1640
  • 12
  • [ 127-63-9 ]
  • [ 2359-60-6 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 458
  • 13
  • [ 111-24-0 ]
  • [ 106-50-3 ]
  • [ 2359-60-6 ]
Reference: [1] Patent: DE858551, 1951, ,
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