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CAS No. : | 53617-35-9 | MDL No. : | MFCD03274733 |
Formula : | C9H18N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 170.25 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.76 |
TPSA : | 24.5 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.33 cm/s |
Log Po/w (iLOGP) : | 2.2 |
Log Po/w (XLOGP3) : | 0.01 |
Log Po/w (WLOGP) : | -0.69 |
Log Po/w (MLOGP) : | 0.34 |
Log Po/w (SILICOS-IT) : | 1.21 |
Consensus Log Po/w : | 0.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.84 |
Solubility : | 24.8 mg/ml ; 0.146 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.08 |
Solubility : | 143.0 mg/ml ; 0.839 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.27 |
Solubility : | 9.16 mg/ml ; 0.0538 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
93% | With hydrogen In methanol at 20℃; for 18 h; | Example 7; 4-(4-piperidinyl)-morpholine (O) 41.59 g (0.16 Mol) 4-[1-(phenylmethyl)-4-piperidinyl]-morpholine (N) are dissolved in 400 mL methanol, combined with 5.2 g palladium on activated charcoal (10percent) and hydrogenated for 18 hours at ambient temperature with 50 psi hydrogen. The catalyst is filtered off and the filtrate is evaporated down. A colourless oil remains, which crystallises after a short time.Yield: 25.29 g (93percent of theory) |
91% | With hydrogenchloride In methanol | 4-(1-benzyl-piperidin-4-yl)-morpholine (1.56 g, 6.0 mmol) was hydrogenated using Pd(OH)2 (20percent on carbon, 390 mg, 25 wtpercent), 1.7 M HCl (10.6 mL) in methanol (50 mL) at 50° C. for 10 hours. The resulted amine dihydrochloride off-white solid was subjected to free-basing using excess basic resin to give 932 mg (91percent) of 4-piperidin-4-yl-morpholine as waxy crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 3.53 (br s, 4H), 3.30 (v br s, 1H), 2.92 (br d, 1H), 2.41 (s, 4H), 2.35 (m, 2H), 2.12 (br t, 1H), 1.65 (br d, 2H), 1.18 (br q, 2H). MS m/z 171 [M++1]. |
91% | With hydrogenchloride In methanol | 4-(1-benzyl-piperidin-4-yl)-morpholine (1.56 g, 6.0 mmol) was hydrogenated using Pd(OH)2 (20percent on carbon, 390 mg, 25 wt percent), 1.7 M HCl (10.6 mL) in methanol (50 mL) at 50° C. for 10 hours. The resulted amine dihydrochloride off-white solid was subjected to free-basing using excess basic resin to give 932 mg (91percent) of 4-piperidin-4-yl-morpholine as waxy crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 3.53 (br s, 4H), 3.30 (v br s, 1H), 2.92 (br d, 1H), 2.41 (s, 4H), 2.35 (m, 2H), 2.12 (br t, 1H), 1.65 (br d, 2H), 1.18 (br q, 2H). MS m/z 171 [M++1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With trifluoroacetic acid In dichloromethane at 20℃; for 6 h; | (0766) Tert-butyl 4-morpholinopiperidin-1-carboxylate (3.0 g, 11.1 mmol) was dissolved in dichloromethane (30 mL), and trifluoroacetic acid (5 mL) was added. The mixture was stirred at room temperature for 6 h, and the solvent was removed under reduced pressure. Saturated sodium bicarbonate solution was added dropwisely to adjust pH of the mixture to pH=8. The mixture was extracted with ethyl acetate (50 mL×3). The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated to get the title compound (1.5 g, yield: 79percent). |
1.52 g | With hydrogenchloride In methanol at 40℃; for 12 h; | Reference Example 20 Synthesis of 4-(morpholin-4-yl)piperidine (0395) (0396) Morpholine (0.792 g, 9.09 mmol), sodium triacetoxyborohydride (1.93 g, 9.09 mmol), and acetic acid (0.0460 g, 0.758 mmol) were added to a solution of 1-tert-butoxycarbonyl-4-piperidinone (1.51 g, 7.58 mmol) in dichloromethane (25.0 mL) at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in hydrochloric acid (1.0 N), and the resulting mixture was extracted with ethyl acetate. A 48percent aqueous solution of sodium hydroxide was added to the aqueous layer for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), and concentrated hydrochloric acid (5.0 mL) was added, and then the resulting mixture was stirred at 40° C. for 12 hours. The reaction liquid was concentrated and exsiccated, and then the residue was dissolved in distilled water. A 48percent aqueous solution of sodium hydroxide was added for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. 4-(Morpholin-4-yl)piperidine (1.52 g, 5.63 mmol, 74percent) was obtained as a yellow solid. (0397) 1H-NMR (400 MHz, CDCl3) δ: 1.34 (2H, dd, J=12.0, 4.0 Hz), 1.40 (2H, dd, J=12.0, 4.0 Hz), 1.85 (2H, d, J=12.4 Hz), 2.28 (1H, tt, J=11.2, 4.0 Hz), 3.53-3.63 (6H, m), 3.15 (2H, d, J=12.4 Hz), 3.73 (4H, t, J=4.4 Hz). (0398) ESI-MS: m/z=171 (M+H)+ |
3 g | With trifluoroacetic acid In dichloromethane at 20℃; | To a stirred solution of tert-butyl 4-morpholinopiperidine-1-carboxylate (step 3, 4.0 g,14.848 mmol, 1.0 eq) in DCM (40 mL) was added TFA (20 mL). The reaction mixture wasstirred at room temperature for overnight. After completion of the reaction (monitored byTLC), the reaction mixture was evaporated under reduced pressure then pH adjusted to 8.05 with saturated NaHC03 solution and extracted with 10percent methanol in DCM (2x50 mL). Thecombined organic layer was dried over sodium sulfate, filtered and evaporated under reducedpressure to obtain the title compound (3.0 g) as a solid. 1H NMR (300 MHz, DMSO-d6): 8ppm 3.55 (t, J = 4.5 Hz, 4H), 3.02-2.94 (m, 2H), 2.44-2.39 (m, 4H), 2.26-2.12 (m, lH), 2.07(m, 2H), 1.73-1.64 (m, 2H), 1.32-1.16 (m, 2H); ESI-MS: m/z 171.03 (M+Ht |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃; for 16 h; | Morpholine (0.792 g, 9.09 mmol), sodium triacetoxyborohydride (1.93 g, 9.09 mmol), and acetic acid (0.0460 g, 0.758 mmol) were added to a solution of 1-tert-butoxycarbonyl-4-piperidinone (1.51 g, 7.58 mmol) in dichloromethane (25.0 mL) at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in hydrochloric acid (1.0 N), and the resulting mixture was extracted with ethyl acetate. A 48percent aqueous solution of sodium hydroxide was added to the aqueous layer for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), and concentrated hydrochloric acid (5.0 mL) was added, and then the resulting mixture was stirred at 40° C. for 12 hours. The reaction liquid was concentrated and exsiccated, and then the residue was dissolved in distilled water. A 48percent aqueous solution of sodium hydroxide was added for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. 4-(Morpholin-4-yl)piperidine (1.52 g, 5.63 mmol, 74percent) was obtained as a yellow solid. |
74% | With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃; for 16 h; | Morpholin (0.792 g, 9.09 mmol), sodium triacetoxyborohydride (1.93 g, 9.09 mmol), acetic acid (0.0460 g, 0.758 mmol) were added to a solution of 1-tert-butoxycarbonyl-4-piperidinone (1.51 g, 7.58 mmol) in dichloromethane (25.0 mL) at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in hydrochloric acid (1.0 N), and the resulting mixture was extracted with ethyl acetate. A 48percent aqueous solution of sodium hydroxide was added to the aqueous layer for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (25.0 mL), and concentrated hydrochloric acid (5.0 mL) was added, and then the resulting mixture was stirred at 40° C. for 12 hours. The reaction liquid was concentrated and exsiccated, and then the residue was dissolved in distilled water. A 48percent aqueous solution of sodium hydroxide was added for basification, and then the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. 4-(Piperidin-4-yl) morpholin (1.52 g, 5.63 mmol, 74percent) was obtained as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 1.34 (2H, dd, J=12.0, 4.0 Hz), 1.40 (2H, dd, J=12.0, 4.0 Hz), 1.85 (2H, d, J=12.4 Hz), 2.28 (1H, tt, J=11.2, 4.0 Hz), 3.53-3.63 (6H, m), 3.15 (2H, d, J=12.4 Hz), 3.73 (4H, t, J=4.4 Hz). ESI-MS: m/z=171 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 20℃; for 1 h; | To a stirred solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (Aldrich, 3.0 g, 15 mmol) in THF (25 mL), morpholine (Aldrich, 1.56 g, 18 mmol) and Ti(OiPr)4 (Aldrich, 5.58 mL) were added successively and the mixture was stirred at room temperature for 1 hour. Then, 15 mL of ethanol was added and followed by sodium cyanoborohydride (0.63 g, 10.05 mmol). The resulting mixture was stirred at room temperature over night and the reaction was quenched with addition of water (4 mL). The mixture was stirred for 30 minutes and the white solid was filtered out and the filtrate was evaporated. The residue was partitioned between ether and water and the organic layer was separated and dried with sodium sulfate. Removal of solvent gave a white solid which was treated with 40 mL of 50percent TFA in methylene chloride. The solution was stirred at room temperature for 1 hour and the solvent was removed. The residue was lyophilized to give a white solid. 5.48 g, 98percent. MS (m+H)+: 171. |
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