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| | 1-BOC-ISONIPECOTIC ACID HYDRAZIDE Basic information | | Uses |
| Product Name: | 1-BOC-ISONIPECOTIC ACID HYDRAZIDE | | Synonyms: | TERT-BUTYL 4-(HYDRAZINOCARBONYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE;1-BOC-ISONIPECOTIC ACID HYDRAZIDE;1-Boc-piperidine-4-carboxylhydrazide;N-Boc-piperidine-4-carboxylhydrazide;1-(tert-Butoxycarbonyl)piperidine-4-carbohydrazide;Isonipecotic acid hydrazide, N1-BOC protected, 4-(Hydrazinocarbonyl)piperidine, N1-BOC protected, tert-Butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate;1-Boc-piperidine-4-carboxylic acid hydrazide;1-Boc-4-(hydrazinocarbonyl)piperidine | | CAS: | 187834-88-4 | | MF: | C11H21N3O3 | | MW: | 243.3 | | EINECS: | | | Product Categories: | | | Mol File: | 187834-88-4.mol |  |
| | 1-BOC-ISONIPECOTIC ACID HYDRAZIDE Chemical Properties |
| Melting point | 104-106°C | | Boiling point | 409.2±34.0 °C(Predicted) | | density | 1.147±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | | form | crystalline solid | | pka | 13.01±0.20(Predicted) | | color | White | | InChI | InChI=1S/C11H21N3O3/c1-11(2,3)17-10(16)14-6-4-8(5-7-14)9(15)13-12/h8H,4-7,12H2,1-3H3,(H,13,15) | | InChIKey | JLIKTOWFNQDEME-UHFFFAOYSA-N | | SMILES | C1C(C(NN)=O)CCN(C(=O)OC(C)(C)C)C1 |
| Hazard Codes | Xi,Xn | | Risk Statements | 22 | | HazardClass | IRRITANT | | HS Code | 2933399990 |
| | 1-BOC-ISONIPECOTIC ACID HYDRAZIDE Usage And Synthesis |
| Uses | Ethyl N-Boc-4-piperidinecarboxylate is a key intermediate in the synthesis of sodium channel blockers used to treat stroke patients. It is also a key intermediate in the preparation of tumor necrosis factor converting enzyme inhibitors. Furthermore, it is a key intermediate in the synthesis of 1-BOC-4-piperidinecarboxylhydrazide. | | Synthesis | The general procedure for the synthesis of 1-BOC-4-piperidinecarbohydrazide from ethyl N-Boc-4-piperidinecarboxylate is as follows:
Example 4: Synthesis of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate
1. 10.0 g (38.9 mmol) of 4-tert-butyl 4-ethylpiperidine-1,4-dicarboxylate was dissolved in 35 mL of ethanol and 3.8 mL (3.90 g, 78 mmol) of hydrazine hydrate was added slowly under stirring conditions.
2. The reaction mixture was heated to reflux with continuous stirring for 9 hours.
3. Upon completion of the reaction, the mixture was cooled to room temperature, 1.9 mL (39 mmol) of hydrazine hydrate was added, and stirring was continued at reflux for 24 hours.
4. At the end of the reaction, the solvent was removed by concentration under reduced pressure and concentrated again by adding 50 mL of ethanol.
5. 150 mL of ether was added to the concentrate and the mixture was sonicated in an ultrasonic bath for 5 minutes.
6. The solid product was collected by filtration and dried to give 9.20 g of white solid in 97% yield.
Product Characterization.
LCMS (Method 6): Rt = 0.95 min, m/z = 244 (M+H)+
1H-NMR (400 MHz, DMSO-d6): δ = 8.99 (s, 1H), 4.17 (br, 2H), 3.95 (br d, 2H), 2.71 (br, 2H), 2.23 (m, 1H), 1.60 (m, 2H), 1.40 (m, 11H). | | References | [1] MedChemComm, 2018, vol. 9, # 12, p. 2083 - 2090
[2] Patent: US2011/144131, 2011, A1. Location in patent: Page/Page column 29
[3] Patent: WO2008/11130, 2008, A2. Location in patent: Page/Page column 151
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4430 - 4448
[5] Patent: WO2018/37223, 2018, A1. Location in patent: Page/Page column 147; 148 |
| | 1-BOC-ISONIPECOTIC ACID HYDRAZIDE Preparation Products And Raw materials |
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