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CAS No. : | 3202-33-3 |
Formula : | C11H15NO |
M.W : | 177.24 |
SMILES Code : | C1CC(CCN1)OC1=CC=CC=C1 |
MDL No. : | MFCD04114971 |
InChI Key : | KBYPITRKIJKGMD-UHFFFAOYSA-N |
Pubchem ID : | 18878 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.45 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 56.76 |
TPSA ? Topological Polar Surface Area: Calculated from | 21.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.02 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.73 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.95 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.42 |
Solubility | 0.672 mg/ml ; 0.00379 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.09 |
Solubility | 1.43 mg/ml ; 0.00806 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.34 |
Solubility | 0.0803 mg/ml ; 0.000453 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -5.95 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.27 |
* 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 |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 16h; | 4-Phenoxypiperidine (0.15g) was added to a solution of the product from step (i) (0.2g), [N,] N-diisopropylethylamine (1. [47ML)] in tetrahydrofuran and stirred at room temperature for 16h. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with ether/isohexane (1: 2). Yield 0.3g white solid. The solid was dissolved in N, [N-DIMETHYLFORMAMIDE] [(20ML),] sodium cyanide [(0.] lg) added and heated at [90C] for 32h. The mixture was partitioned between ethyl acetate and water, the organic layer separated, washed with water, brine, dried (MgS04) and evaporated under reduced pressure. The residue was purified by RPHPLC 35-95% acetonitrile in aqueous [TRIFLUOROACETIC] acid. Yield 0.079g MS: APCI (+ve) 367 (+H) [1HNMR] : (DMSO-d6) 8 7.31-6. 91 (5H, [M),] 4.66 [(1H,] [M),] 4.11-4. 04 (2H, [M),] 3.70- 3.57 [(10H,] [M),] 2.00-1. 95 (2H, m), 1.63-1. 60 (2H, [M)] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 6h; | The product from example 2 step a) (0.24g) and 4-PHENOXYPIPERIDINE (0. 18G) in NMP (5ML) and Hunigs base (0. 5ML) were heated at 100 C FOR 6h. The mixture was cooled and partitioned between ether and water. The phases were separated and the ether phase was dried (NA2SO4) and concentrated in vacuo. The resultant gum was purified by reverse phase HPLC (Symmetry, 75-5% aqueous, ammonium acetate (0.2% aq. ) in acetonitrile) to yield a gum, which on treatment with ethereal HC1 gave the title compound as a pale yellow solid (0.15g). MS (APCI+) 386 [M+H] + 'H NMR 6 (DMSO) 8.39 (d, LH), 7.92 (d, LH), 7.29 (ddt, 2H), 7.00 (dd, 2H), 6.93 (dt, LH), 4.64 (quintet, LH), 3.69 (dd, 2H), 3.47 (dd, 4H), 3.26 (ddd, 2H), 2.12-2. 03 (m, 2H), 1.91- 1.70 (m, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 16h; | The product of example 1 step b) (0. LUG), <strong>[3202-33-3]4-phenoxypiperidine</strong> (O. LG) and Hunigs base (0. 2ML) in NMP (5ML)) were heated at 140 C for 16h. The resulting mixture was concentrated in vacuo and purified by reverse phase HPLC (Symmetry, gradient 75- 5% aqueous, ammonium acetate (0.2% aq. ) in acetonitrile) to give the title compound as a solid (70mg). MS (APCI+) 352 [M+H] + 1H NMR 6 (CDC13) 8. 42 (d, lH), 7.75 (dd, lH), 7.30 (t, 2H), 7.00-6. 91 (m, 3H), 6.66 (d, LH), 4.62-4. 58 (m, LH), 4.00-3. 90 (m, 2H), 3.70-3. 50 (d, 6H), 2.10-1. 80 (m, 8H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | EXAMPLE 16 1-(2-Amino-benzothiazol-6-yl)-2-(4-phenoxy-piperidin-1-yl)-ethane Operating as in example 15, but employing <strong>[3202-33-3]4-phenoxy-piperidine</strong> instead of 4-benzyl-piperidine, the title compound was obtained in 75% yield, m.p. 164-167 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Pd-C; In methanol; acetone; | EXAMPLE 5 4-Phenoxy-1-[(4-fluorophenoxy)propyl]piperidine STR42 A mixture of 4-phenoxypyridine and benzylbromide in acetone was stirred overnight at room temperature. After removal of the solvent, the residue was dissolved in methanol, cooled to -20 C. and treated portionwise with sodium borohydride, and warmed to 0 C. After a standard workup and purification, the resulting tetrahydropyridine adduct was dissolved in methanol and hydrogenated using 20% Pd-C as a catalyst to provide 4-phenoxypiperidine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; | A mixture of <strong>[3202-33-3]4-phenoxypiperidine</strong> and 1-bromo-3-(4-fluorophenoxy)propane in acetone with excess potassium carbonate was heated at reflux for 12 hours to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 4-(S)-oxiranylmethoxy-1H-indole; | EXAMPLE 38 Preparation of (2S)-(-)-1-(4-indolyloxy)-3-(4-phenoxypiperidin-1-yl)-2-propanol ethanedioate The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and <strong>[3202-33-3]4-(phenoxy)piperidine</strong>. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 69% overall yield. FDMS m/e=366 (M+ of free base). | |
In 4-(S)-oxiranylmethoxy-1H-indole; | Example 38 Preparation of (2S)-(-)-1-(4-indolyloxy)-3-(4-phenoxypiperidin-1-yl)-2-propanol ethanedioate The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and <strong>[3202-33-3]4-(phenoxy)piperidine</strong>. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 69% overall yield. FDMS m/e=366 (M+ of free base). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 5 - 20℃; for 16h; | Example 160: 2-(6-Chlorobenzo[b1thiophene-2-carboxarnido)-5-(<strong>[3202-33-3]4-phenoxypiperidine</strong>-1- carbonvDbenzoic acidMethod 8A solution of t-butyl 5-methoxycarbonyl-2-nitrobenzoate (1 eq.) in THF-water (3:1) was treated with LiOH (1.1 eq.) and stirred over night at room temperature. The organic solvent was evaporated under vacuum, a small amount of water was added to obtain solution and the pH was adjusted to 6-7. The aqueous mixture was extracted with ethyl acetate, the organic layer was dried and concentrated under vacuum to afford a residue which was dissolved in MeOH and hydrogenated for 20 h in the presence of 10% palladium on carbon. After filtration of the catalyst through a Celite pad, the filtrate was concentrated under vacuum to afford t-butyl 2-amino-5-carboxybenzoate in 80% yield. This compound was dissolved in THF, 6-chlorobenzo[b]thiophenecarbonyl chloride (1.1 eq.) was added and the reaction mixture was refluxed for 14 h, cooled and concentrated under vacuum. The obtained residue was dissolved in DMF, <strong>[3202-33-3]4-phenoxypiperidine</strong> (1.2 eq.), EDCI (1.5 eq.), HOBt (0.5 eq.) and DIEA (2.5 eq.) were added at 5-10C, and stirring was continued at room temperature for 16 h. The reaction mixture was diluted with water and the precipitated solid was collected by suction filtration and dried. The compound was dissolved in dichloromethane, treated with TFA and stirred for 1 h at room temperature. Concentration of reaction mixture under vacuum and trituration with diethyl ether afforded the title compound, mp > 200C, in 27% overall yield.1 H-NMR (400 MHz, DMSO-d6, 300K), delta ppm: 12.70 (br.s, 1 H), 8.61 (m, 1 H), 8.28 (m, 1 H), 8.12-8.08 (m, 3H), 7.73 (m, 1 H), 7.53 (m, 1 H), 7.55-7.51 (m, 2H), 6.99 (m, 2H), 6.92 (m, 1 H), 4.67 (m, 1 H), 4.20-3.30 (m, 4H), 1.98 (m, 2H), 1.56 (m, 2H).MS, m/z = 535.3 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With N-ethyl-N,N-diisopropylamine; In toluene; at 20℃; for 12h; | General procedure: To a solution of 4-Phenoxypiperidine (333 mg, 1.88 mmol), N,N?-diisopropylethylamine (320 mul, 1.88 mmol) in toluene (3 ml) was added trans-2-phenylcyclopropyl isocyanate (racemic) (300 mg, 1.88 mmol), and the mixture was stirred for 12 h at room temperature. The reaction mixture was then poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (3) (309 mg, 49%) as a white solid. |
Tags: 3202-33-3 synthesis path| 3202-33-3 SDS| 3202-33-3 COA| 3202-33-3 purity| 3202-33-3 application| 3202-33-3 NMR| 3202-33-3 COA| 3202-33-3 structure
A147520 [1171992-10-1]
3-Phenoxypiperidine hydrochloride
Similarity: 0.87
A202269 [21767-15-7]
3-Phenoxypyrrolidine hydrochloride
Similarity: 0.83
A884540 [358789-72-7]
4-((1-Methylpiperidin-4-yl)oxy)aniline
Similarity: 0.82
A153864 [287952-67-4]
4-(4-Trifluoromethoxyphenoxy)piperidine
Similarity: 0.79
A319638 [63843-58-3]
4-(4-Bromophenoxy)piperidine hydrochloride
Similarity: 0.79
A147520 [1171992-10-1]
3-Phenoxypiperidine hydrochloride
Similarity: 0.87
A202269 [21767-15-7]
3-Phenoxypyrrolidine hydrochloride
Similarity: 0.83
A884540 [358789-72-7]
4-((1-Methylpiperidin-4-yl)oxy)aniline
Similarity: 0.82
A153864 [287952-67-4]
4-(4-Trifluoromethoxyphenoxy)piperidine
Similarity: 0.79
A319638 [63843-58-3]
4-(4-Bromophenoxy)piperidine hydrochloride
Similarity: 0.79
A147520 [1171992-10-1]
3-Phenoxypiperidine hydrochloride
Similarity: 0.87
A884540 [358789-72-7]
4-((1-Methylpiperidin-4-yl)oxy)aniline
Similarity: 0.82
A153864 [287952-67-4]
4-(4-Trifluoromethoxyphenoxy)piperidine
Similarity: 0.79
A319638 [63843-58-3]
4-(4-Bromophenoxy)piperidine hydrochloride
Similarity: 0.79
A127131 [400729-14-8]
Spiro[chroman-2,4'-piperidine] hydrochloride
Similarity: 0.75
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H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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The concentration of the dissolution solution you need to prepare is mg/mL