1159825-25-8|4-(3-Bromophenyl)piperidine hydrochloride| Ambeed

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Quality Control of [ 1159825-25-8 ] Purity: 97% SDS Specification

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Product Details of [ 1159825-25-8 ]

CAS No. :	1159825-25-8
Formula :	C₁₁H₁₅BrClN
M.W :	276.60
SMILES Code :	BrC1=CC(C2CCNCC2)=CC=C1.[H]Cl
MDL No. :	MFCD09878769
InChI Key :	ASSSYFRUQWDFMT-UHFFFAOYSA-N
Pubchem ID :	46735221

Safety of [ 1159825-25-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1159825-25-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.45
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	69.9
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	3.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.34
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.	3.34
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	3.41
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.72

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.03
Solubility	0.0258 mg/ml ; 0.0000933 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.47
Solubility	0.0944 mg/ml ; 0.000341 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	-4.46
Solubility	0.00948 mg/ml ; 0.0000343 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
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	Yes
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.	-5.48 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	1.0
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)	1.57

Application In Synthesis of [ 1159825-25-8 ]

* 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 [ 1159825-25-8 ]

[ 1159825-25-8 ] Synthesis Path-Downstream 1~35

1
[ 50-00-0 ]
[ 1159825-25-8 ]
[ 1257704-93-0 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 4-(3-bromo-phenyl)-piperidine; hydrochloride (1.0 g, 3.6 mmol), 37% formaldehyde in water(3.7 mL, 120 mmol), Acetic acid (0.25 mL, 4.4 mmol) and methanol (20 mL) was stirred for 15 minutes at room temperature. The mixture was cooled to 100C in an ice/water bath. Sodium cyanoborohydride (3.0 g, 48 mmol) was added portionwise. A mild exotherm was noted. The mixture was stirred and warmed to room temperature over 18 hours. The mixture was poured into saturated aqueous ammonium chloride (200 mL) and stirred for 1 hour at room temperature. The mixture was extracted with dichloromethane (3 x 75 ml). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to an oil. The residue was triturated in ether (200 mL) and filtered. The filtrate was evaporated to an oil (0.585 g). The oil was dissolved in ether and stirred. Hydrogen chloride (2.0M in ether, 2.0 mL) was added dropwise and stirrred for 30 minutes. The precipitate was filtered and rinsed with ether. 4- (3-Bromo-phenyl)-l-methyl-piperidine hydrochloride was isolated as a crude white solid (0.432 g, 41%). 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 10.52 (s, IH), 7.47-7.41 (m, 2H), 7.37-7.21 (m, 2H), 3.52-3.41 (m, 2H), 3.10-2.95 (m, 2H), 2.85-2.78 (m, IH), 2.75 (s, 3H), 2.15-2.78 (m, 4H). MS = 254, 256 (MH)+.

References: [1]Patent: WO2010/141796,2010,A2 .Location in patent: Page/Page column 220; 221.

2
[ 1159825-25-8 ]
[ 1215013-75-4 ]
[ 1215011-28-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 130℃;	EXAMPLE DDD87768 3'-Piperidin-4-yl-biphenyl-4-sulfonic acid (1,3,5-trimethyl-1H-pyrazol-4-yl)-amide Prepared from the sulphonamide of intermediate 32 (500 mg, 1.28 mmol), <strong>[1159825-25-8]4-(3-bromophenyl)piperidine hydrochloride</strong> (425 mg, 1.54 mmol), tribasic potassium phosphate (652 mg, 3.0 mmol), and Pd(dppf)Cl2.DCM (100 mg, 0.12 mmol) in DMF (3.0 ml) and water (0.75 ml), according to the method of intermediate 11, to give the title compound as an off-white powder (350 mg, 0.82 mmol, 64%). deltaH (D-6 DMSO, 300K) 7.90 (2H, d J 8.4 Hz), 7.71 (2H, d 8.4 Hz), 7.61 (1H, s), 7.58 (1H, d J 7.9 Hz), 7.46 (1H, t J 7.7 Hz), 7.33 (1H, d J 7.7 Hz), 3.58 (3H, s), 3.10-3.07 (2H, m br), 2.70 (1H, tt J 12.1 Hz 3.3 Hz), 2.63 (2H, td 10.8 Hz 1.8 Hz), 1.85 (3H, s), 1.79-1.73 (2H, m br), 1.63 (3H, s), 1.62 (qd J 12.2 Hz 3.8 Hz). m/z (ES+, 70V) 425.2 (MH+).

References: [1]Patent: US9156811,2015,B2 .Location in patent: Page/Page column 55.

3
[ 1159825-25-8 ]
[ 1215013-76-5 ]
[ 1215011-37-2 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 130℃; for 1h;Microwave irradiation;	EXAMPLE DDD88003 3'-Piperidin-4-yl-biphenyl-4-sulfonic acid (2-methyl-pyridin-3-yl)-amide Prepared from the sulphonamide of intermediate 33 (230 mg, 0.62 mmol), <strong>[1159825-25-8]4-(3-bromophenyl)piperidine hydrochloride</strong> (204 mg, 0.74 mmol), tribasic potassium phosphate (313 mg, 1.48 mmol), and Pd(dppf)Cl2.DCM (50 mg, 0.06 mmol) in DMF (3.0 ml) and water (1.0 ml), according to the method of intermediate 11, to give the title compound as an off-white powder (67 mg, 0.16 mmol, 26%). deltaH (CDCl3, 300K) 8.35 (1H, dd J 1.3 Hz 4.7 Hz), 7.76 (2H, d J 8.5 Hz), 7.75 (1H, m), 7.43-7.38 (3H, m), 7.28 (1H, m), 7.15 (1H, dd J 4.7 Hz 8.0 Hz), 3.23-3.18 (2H, m), 2.76 (2H, td J 2.1 Hz 12.1 Hz), 2.68 (1H, tt J 3.6 Hz 12.1 Hz), 2.22 (3H, s), 1.89-1.83 (2H, m br), 1.69 (2H, qd J 12.1 Hz 3.9 Hz). m/z (ES+, 70V) 408.2 (MH+).

References: [1]Patent: US9156811,2015,B2 .Location in patent: Page/Page column 57; 58.

4
[ 1159825-25-8 ]
[ 1215013-77-6 ]
[ 1215011-47-4 ]

Yield	Reaction Conditions	Operation in experiment
12%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 130℃;	EXAMPLE DDD88189 3'-Piperidin-4-yl-biphenyl-4-sulfonic acid (3,5-dimethyl-isoxazol-4-yl)-amide Prepared from the sulphonamide of intermediate 34 (151 mg, 0.4 mmol), <strong>[1159825-25-8]4-(3-bromophenyl)piperidine hydrochloride</strong> (133 mg, 0.48 mmol), tribasic potassium phosphate (144 mg, 0.68 mmol), and Pd(PPh3)4 (48 mg, 0.042 mmol) in DMF (3.2 ml) and water (0.8 ml), according to the method of intermediate 11, to give the title compound as a white solid (19 mg, 0.046 mmol, 12%). deltaH (D-6 DMSO, 300K) 7.00, (4H, s), 6.76 (1H, s), 6.74 (1H, d J 7.7 Hz), 6.64 (1H, t J 6.6 Hz), 6.53 (1H, d J 6.9 Hz), 2.46 (2H, d 12.0 Hz), 2.05 (3H, m), 1.25 (1H, s), 1.19 (3H, s), 1.15 (2H, m), 1.10 (3H, s), 0.99 (2H, q, J=12.2 Hz). m/z (ES+, 70V) 412.2 (MH+).

References: [1]Patent: US9156811,2015,B2 .Location in patent: Page/Page column 59; 60.

5
[ 1159825-25-8 ]
[ 1215013-78-7 ]
3,5-dichloro-3'-(piperidin-4-yl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 130℃; for 1h;Microwave irradiation;	EXAMPLE DDD86470 2,6-Dichloro-N-(3,5-dimethyl-isoxazol-4-yl)-4-(2-piperazin-1-yl-pyridin-4-yl)-benzenesulfonamide Prepared from the boronic ester of intermediate 35 (184 mg, 0.4 mmol), <strong>[1159825-25-8]4-(3-bromophenyl)piperidine hydrochloride</strong> (133 mg, 0.48 mmol), tribasic potassium phosphate (144 mg, 0.68 mmol), and Pd(PPh3)4 (48 mg, 0.042 mmol) in DMF (3.2 ml) and water (0.8 ml), according to the method of intermediate 11, to give the title compound as a yellow solid (20 mg, 0.040 mmol, 16%). deltaH (CDCl3, 300K) 7.63 (2H, s), 7.41 (3H, m), 7.33 (1H, d J 6.6 Hz), 3.68 (3H, s), 3.23 (2H, d J 12.0 Hz), 2.78 (2H, dt J 12.1 Hz 2.1 Hz), 2.71 (1H, tt J 12.1 Hz 3.6 Hz), 2.18 (3H, s), 1.88 (2H, d J 12.6 Hz), 1.73 (3H, s), 1.70 (2H, qd J 12.5 Hz 3.8 Hz). m/z (ES+, 70V) 493.1 (MH+).

References: [1]Patent: US9156811,2015,B2 .Location in patent: Page/Page column 49.

6
[ 843646-72-0 ]
[ 1159825-25-8 ]
2-(3'-(piperidin-4-yl)-[1,1'-biphenyl]-3-yl)acetamide [ No CAS ]