34595-26-1|2-(Piperidin-1-yl)benzaldehyde| Ambeed

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Quality Control of [ 34595-26-1 ] Purity: 97% SDS Specification

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Product Details of [ 34595-26-1 ]

CAS No. :	34595-26-1
Formula :	C₁₂H₁₅NO
M.W :	189.25
SMILES Code :	C1=CC=CC(=C1N2CCCCC2)C=O
MDL No. :	MFCD03419311
InChI Key :	SMABIQIPGVQEEX-UHFFFAOYSA-N
Pubchem ID :	2062157

Safety of [ 34595-26-1 ]

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

Computational Chemistry of [ 34595-26-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	61.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.24
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	2.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.11
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.	1.92
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	2.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.27

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.68
Solubility	0.396 mg/ml ; 0.00209 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.	-2.42
Solubility	0.726 mg/ml ; 0.00383 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	-3.07
Solubility	0.16 mg/ml ; 0.000847 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	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	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	Yes
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	No
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.	-5.79 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	1.0 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)	1.29

Application In Synthesis of [ 34595-26-1 ]

* 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 [ 34595-26-1 ]

[ 34595-26-1 ] Synthesis Path-Downstream 1~35

1
[ 495-69-2 ]
[ 34595-26-1 ]
[ 58028-82-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1975,p. 1679 - 1682.

2
[ 110-89-4 ]
[ 446-52-6 ]
[ 34595-26-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 130℃; for 3h;	To a solution of the aldehyde 3a (20 g, 161.1 mmol) in dry DMF (160 ml), piperidine(19.1 ml, 193.4 mmol, 1.2 eq) and potassium carbonate (26.73 g, 193.4 mmol, 1.2eq) were successively added. The suspension was heated at 130C for 3 h. Thereaction mixture was then poured into cold water and. acidified with citric acid up to ,pH 5. The aqueous layer was extracted 3X with EtOAc and the combined organicextract was successively washed with water, saturated NaHCO3 and brine. Afterdrying the organic extract over MgSO4, filtration and concentration, the desired 2-piperidinobenzaldehyde 3b was isolated as a red oil (28.23 g, 92% yield).
92.1%	With potassium carbonate; In N,N-dimethyl-formamide; for 15h;Reflux;	62.0 g (0.5 mol, 1.0 eq) of o-fluorobenzaldehyde, 200 g of N,N-dimethylformamide, 138.2 g (1.0 mol, 2.0 eq) of potassium carbonate, and 63.9 g (0.75 mol, 1.5 eq) of piperidine were placed in the reaction flask. The mixture was heated to reflux for 15 hours, and the completion of the reaction was monitored by TLC. The reaction mixture was poured into ice water and extracted with methyl t-butyl ether. The organic layer was combined and concentrated under reduced pressure to give 87.1 g of a yellow oil. HPLC purity 95.3%. The yield was 92.1%.
90.5%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); for 6h;Heating / reflux;	EXAMPLE 1 Preparation of o-piperidino benzaldehyde (8) [0033] A mixture of o-fluorobenzaldehyde (1.24 gm, 10 mmol), potassium carbonate (2.76 gm, 20 mmol), and piperidine (1.7 gm, 20 mmol) was refluxed in dry DMF for 6 hrs. After the completion of reaction DMF was distilled out at vaccum and 5 ml of water was added to the residue and extracted the product with ethyl acetate (10 ml×2). Organic layer was dried over sodium sulphate and evaporated the solvent to afford 1.8 gm of product (8) (90.5%) [0034] 1HNMR CDCl3 (Spectrum 9): 1.68(m, 6H), 3.05(m, 4H), 7.05(m, 2H), 7.45(dd, 1H), 7.75(dd, 1H).

	With potassium carbonate; In N,N-dimethyl-formamide;Reflux;	General procedure: To a solution of 2-fluorobenzaldehyde (4.96 g, 40 mmol) and K2CO3 (6.36 g, 46 mmol) in DMF (40 mL) was added piperidine (4.56 mL, 46 mmol). The resulting reaction mixture was heated under reflux until complete consumption of 2-fluorobenzaldehyde. The reaction mixture was allowed to cool to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with a saturated NH4C1 solution and concentrated under reduced pressure. The product 2-(piperidin-1-yl)benzaldehyde was utilized for next step without purification.
1.72 g	With potassium carbonate; In N,N-dimethyl-formamide; at 110 - 150℃; for 23h;	(1) A suspension of the Compound 1 (1.05 mE), the Compound 2 (1.09 mE), and potassium carbonate (2.76 g) in N,N-dimethylformamide (10 mE) was stirred at 1100 C. for 5 hours, and stirred at 1500 C. for 18 hours. The reaction mixture was allowed to cool to room temperature, and then water and ethyl acetate were added thereto, and the resulting mixture was stirred, and extracted with ethyl acetate. The resulting organic layers were washed with water and saturated brine, dried, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=99: 1 to 88:12) to give the Compound 3 (1.72 g) as a yellow liquid. MS (APCI): mlz 190 [M+H]
1.72 g	With potassium carbonate; In N,N-dimethyl-formamide; at 110 - 150℃; for 23h;	(1) Compound 1 (1.05 mL), Compound 2 (1.09 mL)And potassium carbonate (2.76 g)Of N, N-dimethylformamide (10 mL)The suspension was heated at 110 C. for 5 hours,And the mixture was stirred at 150 C. for 18 hours.The reaction mixture was allowed to cool to room temperature,Water and ethyl acetate were added and stirred,And extracted with ethyl acetate.The organic layer was washed with water and saturated brine,Drying,And concentrated under reduced pressure.The residue was purified by silica gel column chromatographyLomagraphy (hexane: ethyl acetate = 99: 1 to 88: 12)To obtain Compound 3 (1.72 g)As a yellow liquid.

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[ 34595-26-1 ]
[ 83716-77-2 ]