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CAS No. : | 138227-63-1 | MDL No. : | MFCD04115023 |
Formula : | C16H24N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WEIBGUDKHYWNMW-UHFFFAOYSA-N |
M.W : | 292.37 | Pubchem ID : | 22181157 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 87.01 |
TPSA : | 64.79 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.2 cm/s |
Log Po/w (iLOGP) : | 3.04 |
Log Po/w (XLOGP3) : | 2.65 |
Log Po/w (WLOGP) : | 2.67 |
Log Po/w (MLOGP) : | 1.89 |
Log Po/w (SILICOS-IT) : | 1.6 |
Consensus Log Po/w : | 2.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.183 mg/ml ; 0.000626 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.66 |
Solubility : | 0.0637 mg/ml ; 0.000218 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.2 mg/ml ; 0.000684 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.38 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
99% | With hydrogen In methanol at 20℃; for 4 h; | To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)nitrobenzene (11.9 g) obtained in reference example 105 in methanol (100 ml) was added palladium on carbon (1.9 g), and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours. At the end of this time, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:1) as the eluent to afford the title compound (10.7 g, yield: 99 percent) as a pale red solid. 1H NMR (400MHz, CDCl3) δ ppm : 1.46 (9H, s), 1.71 (2H, m), 1.87 (2H, m), 3.27 (2H, m), 3.71 (2H, m), 4.26 (1H, m), 6.63 (2H, d, J=8.5), 6.76 (2H, d, J=8.5). |
95% | With palladium 10% on activated carbon; ammonium formate In methanol at 50℃; Inert atmosphere; Reflux | 4.2.8 Tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (12) In a round bottom flask equipped with a magnetic stirring bar and under nitrogen atmosphere, product 11 (11.42 g, 35.4 mmol) and ammonium formate (21.5 g, 354 mmol) were dissolved in 210 mL of degassed MeOH and the solution was heated to 50 °C. 10percent w/w Palladium on activated charcoal (1.10 g) was added and the reaction mixture was stirred at 90 °C (oil bath temperature, in order to ensure a round-boiling reflux of the reaction mixture, even after development of water as a coproduct of the hydrogenation) for 5 h. Hereafter, the reaction mixture was filtered through a short plug of celite, washed with DCM (100 mL) and evaporated in vacuo to give 9.28 g (32.2 mmol, 95percent yield) of pure 12 as a brown solid (m. p. = 80-81 °C). 1H NMR (300 MHz, CDCl3) δ = 6.77-6.71 (m, 2H); 6.63-6.58 (m, 2H); 4.24 (sept, J = 3.6 Hz, 1H); 3.73-3.65 (m, 2H); 3.46 (bs, 2H); 3.29-3.21 (m, 2H); 1.90-1.81 (m, 2H); 1.73-1.62 (m, 2H); 1.45 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3) δ = 154.9; 150.0; 140.7, 118.3; 116.4; 79.5; 73.7; 40.7 (broad); 30.8; 28.4 ppm. IR (KBr) ν = 3460.0, 3361.6, 2955.4, 1685.1, 1509.9, 1419.4, 1229.0, 1049.6 cm-1. GCMS (EI) m/z = 291 [M+·], 219 [M- iBuO]+, 192 [M- isobutylene - CO2]+ ·, 184 [M- PhNH2, - H2O]+ ·, 128 [M- PhNH2, - H2O - isobutylene]+ ·, 109 [4-aminophenol]+ ·, 84 [M- PhNH2, - H2O - isobutylene - CO2]+ ·. |
93% | With palladium 10% on activated carbon; hydrogen In methanol at 50℃; | A solution of tert—butyl 4—(4—nitrophenoxy)piperidine—1—carboxylate (611 mg, 1.895 mmol) in methanol (60 mL) washydrogenated by H-Cube (10percent Pd/C cartridge, Full H2, 50°C, 1 mL/min) . The reaction mixture was concentrated to dryness under reduced pressure to give the title compound as a pale pink solid (517 mg, 93percent) . ‘H NMR (300 MHz,CDC13) : 3 6.76 (dt, 2H), 6.63 (dt, 2H), 4.26 (sep, 1H),3.71 (ddd, 2H), 3.45 (br s, 2H), 3.26 (ddd, 2H), 1.80—1.95 (m, 2H), 1.61—1.78 (m, 2H), 1.46 (s, 9H) . LCMS(Method C) : = 0.85 mi m/z = 237 [M_tBu+H]+. |
82.3% | With hydrogen In methanol; ethanol at 22℃; for 2 h; | A mixture of 4-(4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (3.15 g, 9.77 mmol) and 10percent wt palladium on carbon (1.01 g) in anhydrous ethanol-methanol (1:1, 100 mL) is stirred vigorously under hydrogen gas at 22°C for 2 hr. Then the palladium on carbon is removed by filtration. The filtrate is concentrated to give a white solid (2.35 g, 82.3 percent yield). |
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