Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 165377-44-6 | MDL No. : | MFCD00939308 |
Formula : | C23H34Cl2N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XWOXAKBQEMQMFH-UHFFFAOYSA-N |
M.W : | 441.43 | Pubchem ID : | 9954941 |
Synonyms : |
SA4503 dihydrochloride;AGY94806 dihydrochloride;Cutamesine;AGY 94806;SA 4503;Cutamesine dihydrochloride
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.48 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 132.77 |
TPSA : | 24.94 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.11 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 5.47 |
Log Po/w (WLOGP) : | 4.34 |
Log Po/w (MLOGP) : | 3.35 |
Log Po/w (SILICOS-IT) : | 4.54 |
Consensus Log Po/w : | 3.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.74 |
Solubility : | 0.000812 mg/ml ; 0.00000184 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.75 |
Solubility : | 0.000783 mg/ml ; 0.00000177 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.92 |
Solubility : | 0.0000528 mg/ml ; 0.00000012 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 2.87 |
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 |
---|---|---|
0.68 g (77%) | With hydrogenchloride; sodium iodide; potassium carbonate In <i>N</i>-methyl-acetamide; ethanol; water | 1 1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (compound No. 1-1) STR9 Example 1 1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (compound No. 1-1) STR9 To a solution of N,N-bis(2-chloroethyl)-2-(3,4-dimethoxyphenyl)ethylamine hydrochloride (reference compound No. 2-1, 0.69 g) and 3-phenylpropylamine (0.41 g) in dimethylformamide (20 ml) were added potassium carbonate (0.83 g) and sodium iodide (0.90 g). The mixture was stirred at 70° C. for 2 hours. To the reaction mixture, water was added, and the whole was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The oily residue was dissolved in ethanol, 6N hydrochloric acid (2 ml) was added thereto, and the solution was concentrated in vacuo to give 0.68 g (77%) of the titled compound (compound No. 1-1). mp 258°-260° C. (decomp.) IR (KBr, cm-1) 3977, 2355, 1518, 1265, 1140, 1028, 754, 704 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In tetrahydrofuran; water | 15 To a suspension of l-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3- phenylpropyl)piperazine dihydrochloride (1.06 g, 2.40 mmol) in THF (5 niL) is added a solution of sodium hydroxide (IN, 6 mL). To the resulting solution is added ethyl acetate and brine. The organic layer is separated, filtered through silica gel, dried over anhydrous sodium sulfate, concentrated, and dried to give 0.829 g of l-[2-(3,4- dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine as a light brown solid.To a solution of l-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine (0.829 g, 2.25 mmol) in dichloromethane (DCM, 20 mL) is added boron tribromide (BBr3) drop wise at -78 °C under nitrogen. After the addition had been completed, the reaction solution is slowly warmed to 0 °C, stirred for 5 h and then cooled to -10 °C. To the cooled reaction mixture is added water cautiously. The resulting mixture is neutralised with sodium bicarbonate at ambient temperature and extracted with ethyl acetate/THF. The organic layer is separated, filtered through silica gel, dried over sodium sulfate, concentrated, and dried in a vacuum oven. . The residue is then purified by column chromatography eluting with dichloromethane-methanol to afford 0.57 g of 1- [2-(3,4-dihydroxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine . This material is then dissolved in ethanol and treated with 6 N hydrogen chloride aqueous solution to pH=3. The resultant crystals are filtered, washed with cold ethanol, and dried to give 212 mg of the title compound (25% from l-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3- phenylpropyl)piperazine dihydrochloride ). 1H-NMR (400MHz, DMSO-d6): δ 2.02 (b, 2H), 2.64 (t, 2H), 2.86 (b, 2H), 3.1-3.8 (m, 12), 6.51 (d, IH), 6.67 (m, 2H), 7.11-7.33 (m, 5H), 8.84 (b, 2H), 11.6 (b, 2H). |