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CAS No. : | 156185-63-6 | MDL No. : | MFCD02677712 |
Formula : | C13H25NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OXPWHPCCUXESFQ-UHFFFAOYSA-N |
M.W : | 243.34 | Pubchem ID : | 2800739 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.92 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 72.18 |
TPSA : | 49.77 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 3.11 |
Log Po/w (XLOGP3) : | 1.89 |
Log Po/w (WLOGP) : | 2.03 |
Log Po/w (MLOGP) : | 1.71 |
Log Po/w (SILICOS-IT) : | 1.71 |
Consensus Log Po/w : | 2.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.14 |
Solubility : | 1.75 mg/ml ; 0.00719 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.56 |
Solubility : | 0.674 mg/ml ; 0.00277 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.92 |
Solubility : | 2.93 mg/ml ; 0.0121 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.3 |
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 |
---|---|---|
88% | at 20℃; for 2 h; | Preparation 144-(3-Aminopropyl)-piperidine-1-carboxylic acid tert-butyl ester(A). Preparation of 4-(3-hydroxypropyl)-piperidine-1-carboxylic acid tert-butyl ester; Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) is added to a stirred solution of 3-piperidin-4-yl-propan-1-ol (1.60 g, 11.2 mmol) in anhydrous dichloromethane (20 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir for 2 hours. The mixture is directly subjected to chromatography purification on silica gel and eluted with MeOH in dichloromethane 0-3percent to give the title compound as a clear oil (2.40 g, 88percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium hydroxide In 1,4-dioxane; water for 2 h; | 3- (N-Boe-Piperidin-4-yl)-propan-1-ol:; crude 3-piperidin-4-yl- propan-l-ol (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 mL) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 mL) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH9. After 2 hours no residual amine was visible by TLC (ninhydrin stain) and the reaction was diluted with water (200 mL)and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MgS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985, 18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane. 3-(N-Boc-Piperidin-4-yl)- propan-1-ol was isolated as a clear, colorless oil (14.5 g, 82percent). 1H NMR (500 MHz, CDC13) D 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1.5 (4H, m), 1.47 (9H, s), 1.4 - 1.3 (5H, m), 1.12 (2H, m). |
82% | With sodium hydroxide In 1,4-dioxane; water for 2 h; | 3-(N-BOC-PIPERIDIN-4-YL)-PROPAN-1-OL : The crude 3-PIPERIDIN-4-YL-PROPAN-1-OL (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 ML) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 ML) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH9. After 2 hours no residual amine was visible by TLC (ninhydrin stain) and the reaction was diluted with water (200 ML) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MGS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985,18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane. 3- (N-Boc-Piperidin-4-yl)- PROPAN-1-OL was isolated as a clear, colorless oil (14.5 g, 82percent). LH NMR (500 MHz, CDCl3) 8 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1. 5 (4H, m), 1.47 (9H, s), 1.4-1. 3 (5H, m), 1.12 (2H, m). |
82% | With sodium hydroxide In 1,4-dioxane; water for 2 h; | Step B: The crude 3-piperidin-4-yl-propan-l-ol (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 mL) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 mL) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH 9. After 2 hours no residual amine was visible by TLC analysis (ninhydrin stain) and the reaction was diluted with water (200 mL) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MgS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985,18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane to afford 3-(N-Boc-piperidin-4-yl)-propan-l-ol as a clear, colorless oil (14.5 g, 82percent). 1H NMR (CDC13) 8 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1.5 (4H, m), 1.47 (9H, s), 1.4 - 1.3 (5H, m), 1.12 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5 g | With diisobutylaluminium hydride In dichloromethane at -78 - 0℃; for 2 h; Inert atmosphere | In a 500-ml flask swept with nitrogen, 5 g (17.53 mmol) of tert-butyl 4-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate (prepared according to the method reported in J. Med. Chem. 1995, 38, p 3332-3341 by taking commercial tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate as the starting product) in 100 ml of dichloromethane. The medium is cooled to -78° C. and 52.6 ml (52.6 mmol) of a 1 M solution of DIBAL-H in dichloromethane are added dropwise. It is stirred for 2 h at 0° C. It is cooled to -78° C. and a saturated solution of potassium sodium tartrate is added. After return to room temperature, it is extracted and then the organic phase is dried on Na2SO4, filtered and evaporated, and 4.5 g of the crude oil are obtained, used as is in the next step. |
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