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CAS No. : | 171049-35-7 | MDL No. : | MFCD02179169 |
Formula : | C15H28N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NERBLCVCQKXTEP-UHFFFAOYSA-N |
M.W : | 268.40 | Pubchem ID : | 11747599 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.93 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 85.23 |
TPSA : | 41.57 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.4 cm/s |
Log Po/w (iLOGP) : | 3.38 |
Log Po/w (XLOGP3) : | 2.17 |
Log Po/w (WLOGP) : | 1.87 |
Log Po/w (MLOGP) : | 2.23 |
Log Po/w (SILICOS-IT) : | 1.93 |
Consensus Log Po/w : | 2.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.61 |
Solubility : | 0.663 mg/ml ; 0.00247 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.68 |
Solubility : | 0.566 mg/ml ; 0.00211 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.48 |
Solubility : | 0.881 mg/ml ; 0.00328 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydroxide In ethanol; water at 0 - 10℃; for 1 h; | PREPARATION LXXXIX; 4-(4-piperidinyl)-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester; A solution is prepared of 41 g (0.17 M) of 4,4'-bipiperidine dihydrochloride in 250 ml of ethanol and 250 ml of 2N sodium hydroxide. A solution of 18.5 g (0.085 M) of t-butyl dicarbonate in 100 ml of ethanol are added slowly, at 0° C. The reaction mixture is agitated for 1 hour at 10° C. and the ethanol is then removed by an evaporator, under reduced pressure. The residual aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v). 16.5 g of the compound sought after are thus obtained as a white solid (yield=72percent). M.Pt.=70-71° C. |
63% | With sodium hydroxide In ethanol; water | PREPARATION 9 Preparation of N-(t-butoxycarbonyl)-4,4'-bipiperidine 4,4'-Bipiperidine dihydrochloride (2.5 g, 10 mmol) was dissolved in water (10 mL) and treated with 5N sodium hydroxide to pH 8-9, diluted to 120 mL with ethanol and stirred at RT. The resulting mixture was treated with di-t-butyl dicarbonate (2.4 g, 11 mmol) in ethanol (80 mL) in one portion and the mixture stirred at RT, with periodic additions of 5N sodium hydroxide to maintain a pH of 8-9. After 5 h. the mixture was concentrated and the residue was dissolved in a mixture of 1:1 ether:water (100 mL) and the pH adjusted to 12 with 5N sodium hydroxide. The aqueous phase was extracted with ether and the organic phase was washed sequentially with brine, dilute citric acid, and water. The aqueous phase was adjusted to pH 12-13 with 5N sodium hydroxide and extracted with ether. The organic phase was washed with brine, dried (sodium sulfate), concentrated to a clear oil and dried in vacuo to give the title compound (1.7 g, 63percent) as a solid. TLC Rf 0.4 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS (ES) m/e 268.3 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | for 8 h; | To 4,4'-bipiperidine (5.48 g, 32.6 mmol) in THF (160 mL) and CHCl3 (160 mL) was added BOC-On (4.01 g) in THF (90 mL) dropwise over a 8 h period. The reaction was then concentrated and purified by flash chromatography. The residue was taken up in 1M KHSO4 (250 mL) and washed with diethyl ether (three times). K2CO3 (38.0 g, 275 mmol) was added to the aqueous layer which was subsequently extracted with CHCl3 (3.x.), dried (MgSO4) and concentrated to provide the title compound of step A (1.98 g, 7.40 mmol, 45percent). 1H NMR (400 MHz, CDCl3) δ ppm 1.06-1.18 (m, 5H), 1.42 (s, 9H), 1.58-1.69 (m, 6H), 2.50-2.61 (m, 4H), 3.06 (d, J=12.1 Hz, 2H), 4.08 (br. s., 2H). |
45% | Stage #1: for 8 h; Stage #2: With potassium hydrogensulfate In water Stage #3: With potassium carbonate In water |
Intermediate B114: 2-(methyloxy)-4-{1'-[2-(methylsulfonyl)ethyl]-4,4'- bipiperidin-1-yl}aniline; Step A/Intermediate B1 15: 1 ,1-dimethylethyl 4,4'-bipiperidine-1-carboxylate; To 4,4'-bipiperidine (5.48 g, 32.6 mmol) in tetrahydrofuran (160 ml.) and chloroform (160 ml.) was added BOC-ON (4.01 g, 16.2 mmol) in tetrahydrofuran (90 ml.) dropwise over an 8 hour period. The reaction was then concentrated and purified by chromatograpy on Siψ2. The residue was taken up in 1 M KHSO4 (250 ml.) and washed with diethyl ether (three times). Potassium carbonate (38.0 g, 275 mmol) was added to the aqueous layer which was subsequently extracted with chloroform (three times), dried (MgSO4), and concentrated to provide 1 ,1-dimethylethyl 4,4'- bipiperidine-1-carboxylate (1.98 g, 7.40 mmol, 45percent). 1 H NMR (400 MHz, CDCI3) δ ppm 1.06 - 1.18 (m, 6 H), 1.42 (s, 9 H), 1.58 - 1.69 (m, 6 H), 2.50 - 2.61 (m, 4 H), 3.06 (d, J=12.1 Hz, 2 H), 4.08 (br s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydroxide In ethanol; water | Preparation 22 Preparation of N-(t-butoxycarbonyl)-4,4'-bipiperdine 4,4'-Bipiperidine dihydrochloride (2.5 g, 10 mmol) was dissolved in water (10 mL) and treated with 5N sodium hydroxide to pH 8-9, diluted to 120 mL with ethanol and stirred at RT. The resulting mixture was treated with di-t-butyl dicarbonate (2.4 g, 11 mmol) in ethanol (80 mL) in one portion and the mixture stirred at RT, with periodic additions of 5N sodium hydroxide to maintain a pH of 8-9. After 5 h, the mixture was concentrated and the residue was dissolved in a mixture of 1:1 ether water (100 mL) and the pH adjusted to 12 with 5N sodium hydroxide. The aqueous phase was extracted with ether and the organic phase was washed sequentially with brine, dilute citric acid, and water. The aqueous phase was adjusted to pH 12-13 with 5N sodium hydroxide and extracted with ether. The organic phase was washed with brine, dried (sodium sulfate), concentrated to a clear oil and dried in vacuo to give the title compound (1.7 g, 63percent) as a solid. TLC Rf 0.4 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS (ES) m/e 268.3 [M+H]+. |
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