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Chemical Structure| 622-26-4 Chemical Structure| 622-26-4

Structure of 4-Piperidineethanol
CAS No.: 622-26-4

Chemical Structure| 622-26-4

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Product Citations

Product Citations

Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing ; Gordon, Akiva ; Jiang, Allen ; Varley, Andrew , et al.

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of [ 622-26-4 ]

CAS No. :622-26-4
Formula : C7H15NO
M.W : 129.20
SMILES Code : OCCC1CCNCC1
MDL No. :MFCD00006008
InChI Key :LDSQQXKSEFZAPE-UHFFFAOYSA-N
Pubchem ID :73953

Safety of [ 622-26-4 ]

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

Computational Chemistry of [ 622-26-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 41.53
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

32.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.77
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.21
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.01
Log Po/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.

0.57
Log Po/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

1.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.75

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.64
Solubility 29.5 mg/ml ; 0.228 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.45
Solubility 46.2 mg/ml ; 0.358 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-1.28
Solubility 6.7 mg/ml ; 0.0519 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

No
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

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.

-6.94 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)

1.0

Application In Synthesis of [ 622-26-4 ]

* 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 [ 622-26-4 ]

[ 622-26-4 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 622-26-4 ]
  • [ 54044-79-0 ]
  • [ 314064-66-9 ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate; at 120℃; A suspension containing <strong>[54044-79-0]2-bromo-5-methyl-1,3,4-thiadiazole</strong> (Modarai, B., et al. J. Heterocyclic Chem. (1974) 11, 343-5) (100 mg, 0.56 mmol), 4-piperidine ethanol (87 mg, 0.67 mmol) and potassium carbonate (77 mg, 0.56 mmol) was heated overnight at 120 C. The reaction was cooled and the mixture partitioned between water (10 ml) and ethyl acetate (30 ml), then the organic layer was washed with brine, dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel (8 g; eluent 2.5% methanol/DCM) gave 1-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(2-hydroxyethyl)piperidine (41 mg, 32%), 1H nmr; 1.33 (m, 2H), 1.54 (q, 2H), 1.7 (m, 1H), 1.79 (m, 2H), 2.54 (s, 3H), 3.08 (m, 2H), 3.71 (t, 2H), 3.88 (m, 2).
  • 3
  • [ 622-26-4 ]
  • [ 2346-26-1 ]
  • 3-(2-piperidin-4-ylethyl)-1,3-oxazolidine-2,4-dione hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 (COMPOUND 25); 2-(methylamino)-2-oxoethyl 2-[1-(biphenyl-4-ylmethyl)piperidin-4-yl]ethylcarbamate; 1.1. 3-(2-piperidin-4-ylethyl)-1,3-<strong>[2346-26-1]oxazolidine-2,4-dione</strong> hydrochloride; A solution of 10 g (77.40 mmol) of 2-piperidin-4-ylethanol, 22.33 g (85.14 mmol) of triphenylphosphine and 9.39 g (92.88 mmol) of 1,3-<strong>[2346-26-1]oxazolidine-2,4-dione</strong> (J. Med. Chem. 1991, 34, 1538-44) in 150 ml of tetrahydrofuran, cooled to approximately -10 C., is admixed dropwise under an inert atmosphere with a solution of 15.65 g (77.40 mmol) of diisopropyl azodicarboxylate (DIAD) in 25 ml of tetrahydrofuran, during which the temperature of the reaction mixture is held between -10 C. and 0 C. Stirring is continued at 0 C. for 1 hour and then at 25 C. for 22 hours. The solid formed is collected by filtration, washed repeatedly with tetrahydrofuran and then dried under vacuum at approximately 70 C. This solid is then taken up in a solution of hydrochloric acid (5N) in isopropanol. The solid formed is collected by filtration and then washed with ethyl acetate and ether. Drying under vacuum at approximately 70 C. gives 6.45 g of hydrochloride in the form of a white solid. M.P. ( C.): 178 C.
  • 4
  • [ 622-26-4 ]
  • [ 1677-80-1 ]
  • [ 1133971-55-7 ]
  • 5
  • [ 622-26-4 ]
  • [ 5467-57-2 ]
  • [ 1312812-97-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 200℃; for 0.5h;Inert atmosphere; Microwave irradiation; A mixture of <strong>[5467-57-2]2-chloroquinoline-4-carboxylic acid</strong> (0.95 g, 4.6 mmol) and 2-(piperidin-4-yl)ethanol (4.72 g, 36.5 mmol) in pyridine (10 mL) was heated to 200 °C for 30 min using a microwave reactor. Toluene was then added and the reaction mixture was concentrated in vacuo to give crude 2-[4-(2-hydroxyethyl)piperidin-1-yl]quinoline-4-carboxylic acid that was used with no further purification. A mixture of crude 2-[4-(2-hydroxyethyl)piperidin-1-yl]quinoline-4-carboxylic acid (4.56 mmol), sulfuric acid (0.97 mL, 18.2 mmol) in MeOH (20 mL) was heated at 120 °C for 30 min using a microwave reactor. Additional sulfuric acid (0.97 mL, 18.2 mmol) was added and the reaction mixture was heated 120 °C for 4 h using a microwave reactor. The reaction mixture was then partially evaporated and the residue partitioned between DCM and saturated aqueous NaHCO3. The aqueous phase was extracted with DCM (three times) and the combined organic phases were dried using a phase separator and concentrated in vacuo to leave a residue. The residue was purified by flash chromatography (50-->100percent EtOAc in heptane) to give methyl 2-[4-(2-hydroxyethyl)piperidin-1-yl]quinoline-4-carboxylate (1.03 g, 72percent). Oxalyl chloride (0.93 mL, 10.5 mmol) was added dropwise to a solution of DMSO (1.5 mL, 21.0 mmol) in DCM (45 mL) at -78 °C and the reaction mixture was stirred at -78 °C for 5 min. A solution of methyl 2-[4-(2-hydroxyethyl)piperidin-1-yl]quinoline-4-carboxylate (1.10 g, 3.51 mmol) in DCM (30 mL) was added and reaction mixture was stirred for 30 min at -78 °C. Triethylamine (6.8 mL, 49.1 mmol) was added and the reaction mixture was allowed to reach rt over 80 min. The reaction mixture was diluted with DCM and washed with H2O. The aqueous phase was extracted with DCM and the combined organic phases were dried (phase separator) and concentrated in vacuo to give the crude methyl 2-[4-(2-oxoethyl)piperidin-1-yl]quinoline-4-carboxylate, that was used with no further purification. Crude methyl 2-[4-(2-oxoethyl)piperidin-1-yl]quinoline-4-carboxylate (3.51 mmol) was dissolved in 2M dimethylamine (30 ml, 60 mmol) in MeOH. After 5 min sodium triacetoxyborohydride (3.72 g, 17.6 mmol) was added and the reaction mixture was stirred at rt for 2h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous phase was extracted with EtOAc (three times) and the combined organic phases were dried (Na2SO4) and concentrated in vacuo to leave a residue which was purified by flash column chromatography (0-->40percent MeOH in DCM) to give the title compound (0.92 g, 76 percent). 1H NMR (600 MHz, CDCl3) delta 8.41 - 8.37 (m, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.55 - 7.52 (m, 1H), 7.29 - 7.24 (m, 1H), 4.54 (d, J = 13.2 Hz, 2H), 4.00 (s, 3H), 3.02 - 2.91 (m, 2H), 2.40 - 2.32 (m, 2H), 2.24 (s, 6H), 1.82 (d, J = 12.4 Hz, 2H), 1.67 - 1.58 (m, 1H), 1.45 (dd, J = 15.0, 7.1 Hz, 2H), 1.33 - 1.24 (m, J = 12.6, 4.0 Hz, 2H); m/z (M+H)+ 342.2.
  • 6
  • [ 622-26-4 ]
  • [ 10241-97-1 ]
  • [ 1126084-77-2 ]
YieldReaction ConditionsOperation in experiment
85% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 14h; To a solution of <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (20) (263mg, 1.50mmol) in THF (7mL) were added 2-(piperidin-4-yl)ethanol (213mg, 1.65mmol), 1-hydroxybenzotriazole (HOBt, 101mg, 0.750mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC) hydrochloride (316mg, 1.65mmol), followed by stirring at room temperature for 14h. The reaction mixture was partitioned between ethyl acetate and 0.5M aqueous hydrochloric acid. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The residue was recrystallized from ethyl acetate/acetonitrile (5mL/2mL) to give 3 (365mg, 85.0percent) as a beige powder. 1H NMR-DMSO-d6 (400MHz) delta 1.11?1.19 (2H, m), 1.38?1.43 (2H, m), 1.73?1.76 (3H, m), 2.36 (3H, s), 2.98 (2H, s), 3.45?3.49 (2H, m), 4.37?4.44 (3H, m), 6.63 (1H, m), 7.00 (1H, m), 7.29 (1H, m), 7.36 (1H, s), 11.38 (1H, s). EI-MS: m/z 286 [M]+. Anal. Calcd for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78. Found: C, 71.10, H, 7.87; N, 9.67.
 

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Technical Information

Categories

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