| Identification | Back Directory | [Name]
1-BOC-ISONIPECOTIC ACID HYDRAZIDE | [CAS]
187834-88-4 | [Synonyms]
KA-0848
-4-(hydrazinocarbonyL
1-boc-isonipecotis acid hydrazide
1-Boc-piperidine-4-carbohydrazide
1-BOC-ISONIPECOTIC ACID HYDRAZIDE
)tetrahydro-1(2H)-pyridinecarboxyL
1-Boc-piperidine-4-carboxylhydrazide
N-Boc-piperidine-4-carboxylhydrazide
1-Boc-4-(hydrazinocarbonyl)piperidine
1-Boc-piperidine-4-carboxylic acid hydrazide
1-(tert-Butoxycarbonyl)piperidine-4-carbohydrazide
tert-butyl 4-(aminocarbamoyl)piperidine-1-carboxylate
tert-butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate
tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate
4-carbazoylpiperidine-1-carboxylic acid tert-butyl ester
4-(hydrazinecarbonyl)-1-piperidinecarboxylic acid tert-butyl ester
TERT-BUTYL 4-(HYDRAZINOCARBONYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
1,4-Piperidinedicarboxylicacid, 1-(1,1-dimethylethyl) ester, 4-hydrazide
Isonipecotic acid hydrazide, N1-BOC protected, 4-(Hydrazinocarbonyl)piperidine, N1-BOC protected, tert-Butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate | [Molecular Formula]
C11H21N3O3 | [MDL Number]
MFCD06795927 | [MOL File]
187834-88-4.mol | [Molecular Weight]
243.3 |
| Chemical Properties | Back Directory | [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 |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [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 |
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