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| | N-Boc-3-Cyanopiperidine Basic information |
| Product Name: | N-Boc-3-Cyanopiperidine | | Synonyms: | 1-N-BOC-PIPERIDINE-3-CARBONITRILE;(+/-)-1-N-BOC-3-CYANO-PIPERIDINE;1-N-BOC-3-CYANOPIPERIDINE;3-CYANO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-Boc-3-cyanopiperdine;1-Piperidinecarboxylic acid, 3-cyano-, 1,1-dimethylethyl este;(R)-N-1-BOC-3-CYANOPIPERDINE;1-N-BOC-3-CYANOPIPERDINE | | CAS: | 91419-53-3 | | MF: | C11H18N2O2 | | MW: | 210.27 | | EINECS: | | | Product Categories: | Piperidine | | Mol File: | 91419-53-3.mol |  |
| | N-Boc-3-Cyanopiperidine Chemical Properties |
| Melting point | 60-65℃ | | Boiling point | 40°C/30mmHg(lit.) | | density | 1.07±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | soluble in Methanol | | pka | -3.42±0.40(Predicted) | | form | Powder | | color | White to yellow | | Sensitive | Moisture Sensitive | | InChI | InChI=1S/C11H18N2O2/c1-11(2,3)15-10(14)13-6-4-5-9(7-12)8-13/h9H,4-6,8H2,1-3H3 | | InChIKey | UEFZTXGFHKPSFS-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCCC(C#N)C1 | | CAS DataBase Reference | 91419-53-3(CAS DataBase Reference) |
| Hazard Codes | Xn,N | | Risk Statements | 22-36/37/38-50 | | Safety Statements | 26-61 | | RIDADR | UN 3077 9 / PGIII | | WGK Germany | 3 | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29335990 |
| | N-Boc-3-Cyanopiperidine Usage And Synthesis |
| Uses | N-Boc-3-Cyanopiperidine is an intermediate used to prepare inhibitors of aurora kinases based on the imidazo-[1,2-a]-Pyrazine core. | | Synthesis | General procedure for the synthesis of tert-butyl 3-cyanopiperidine-1-carboxylate (3) from N-BOC-3-piperidinecarboxamide: To a solution of tert-butyl-3-carbamoylpiperidine-1-carboxylate (2) (1.0 g, 4 mmol) in anhydrous methylene chloride (20 mL) was added triethylamine (3.1 g, 31.0 mmol), followed by a slow, dropwise addition of trifluoroacetic acid anhydride (4.1 g , 20.0 mmol). The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was partitioned between dichloromethane (50 mL) and water (50 mL). The organic phase was washed with saturated sodium bicarbonate solution (100 mL) and subsequently dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give a viscous liquid product 3 (800 mg, 87% yield).1H NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 1.77 (m, 2H), 1.97 (brs, 1H), 2.66 (m, 1H), 3.35-3.84 (brs, 4H). | | References | [1] Patent: US2009/215822, 2009, A1. Location in patent: Page/Page column 11
[2] Patent: WO2006/123257, 2006, A2. Location in patent: Page/Page column 34
[3] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[4] Tetrahedron, 2002, vol. 58, # 18, p. 3561 - 3577
[5] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00606 |
| | N-Boc-3-Cyanopiperidine Preparation Products And Raw materials |
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