4-hydroxy-4-phenylpiperidine
4-hydroxy-4-phenylpiperidine
CAS: 40807-61-2
Molecular Formula: C11H15NO
4-hydroxy-4-phenylpiperidine - Names and Identifiers
| Name | 4-hydroxy-4-phenylpiperidine |
| Synonyms | NSC 71658 4-phenylpiperidin-4-ol LABOTEST-BB LT00233127 Traxoprodil Impurity 3 4-HYDROXY-4-PHENYLPIPERIDINE 4-hydroxy-4-phenylpiperidine 4-Hydroxy-4-phenylpiperadine 4-(4-Phenyl)-4-Hydroxy Piperidine (2-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-yl)-(1-piperidinyl)methanone |
| CAS | 40807-61-2 |
| EINECS | 255-089-0 |
| InChI | InChI=1/C11H15NO/c13-11(6-8-12-9-7-11)10-4-2-1-3-5-10/h1-5,12-13H,6-9H2 |
| InChIKey | KQKFQBTWXOGINC-UHFFFAOYSA-N |
4-hydroxy-4-phenylpiperidine - Physico-chemical Properties
| Molecular Formula | C11H15NO |
| Molar Mass | 177.24 |
| Density | 1.093 |
| Melting Point | 157-161°C(lit.) |
| Boling Point | 317.9°C at 760 mmHg |
| Flash Point | 137.2°C |
| Vapor Presure | 0.000157mmHg at 25°C |
| Appearance | Solid |
| Color | Pale brown |
| BRN | 141577 |
| Storage Condition | 2-8°C(protect from light) |
| Refractive Index | 1.559 |
| MDL | MFCD00006000 |
4-hydroxy-4-phenylpiperidine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
4-hydroxy-4-phenylpiperidine - Reference Information
| Use | 4-phenyl-4-hydroxypiperidine is a pharmaceutical intermediate, which can be made of bromobenzene and Boc-4-piperidone or Cbz-4-piperidone is obtained through a two-step reaction as a raw material. |
| Preparation method | Step A: Add a solution of bromobenzene (1.0 equivalents) in n-BuLi(1.05 equivalents) in THF dropwise to a solution of bromobenzene (equivalents) in anhydrous THF at -78°C. After addition, the mixture was stirred at -78°C for about 0.5 hours. Then, the solution of Boc-4-piperidone in THF was added dropwise by syringe at -78°C. After adding, the resulting mixture was stirred at -78°C at N2 for 2h, and then heated to r.t. The reaction mixture was quenched with a saturated NH4Cl solution, and the resulting mixture was extracted with EtOAc(50mL,30mL). The combined organic phase was washed with brine, dried with anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc) to give the compound 1-BC-4-phenyl-4-hydroxypiperidine. Step B: Add a solution of HCl(3 equivalents) in dioxane to a solution of compound 1-BOC-4-phenyl-4-hydroxypiperidine (1 equivalent) in dioxane, and stir the reaction mixture at room temperature for about 2 hours. At this time, LCMS detects that there is no s.m. Concentrate the reaction mixture to obtain the desired product 4-phenyl-4-hydroxypiperidine. |
Last Update：2024-04-09 21:01:54
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