| Identification | More | [Name]
1-Boc-4-cyanopiperidine | [CAS]
91419-52-2 | [Synonyms]
1-BOC-4-CYANOPIPERIDINE
1-N-BOC-4-CYANO-PIPERIDINE
1-N-BOC-PIPERIDINE-4-CARBONITRILE
4-CYANO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
4-CYANOPIPERIDINE, N-BOC PROTECTED
N-BOC-4-CYANO-PIPERIDINE
TERT-BUTYL 4-CYANOPIPERIDINE-1-CARBOXYLATE
1-Piperidinecarboxylic acid, 4-cyano-, 1,1-dimethylethyl ester
Boc-4-cyanopiperidine
1-BOC-PIPERIDINE-4-CARBONITRILE
N-Boc-piperidine-4-carbonitrile | [Molecular Formula]
C11H18N2O2 | [MDL Number]
MFCD01861223 | [Molecular Weight]
210.27 | [MOL File]
91419-52-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellowish Oil | [Melting point ]
60-63 °C | [Boiling point ]
325.3±35.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Chloroform | [form ]
Crystalline Powder | [pka]
-3.08±0.40(Predicted) | [color ]
White to off-white | [Detection Methods]
GC | [InChI]
InChI=1S/C11H18N2O2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-7H2,1-3H3 | [InChIKey]
UQADQTBQNVARAP-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC(C#N)CC1 | [CAS DataBase Reference]
91419-52-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3439 | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellowish Oil | [Uses]
Reactant for synthesis of:
- Aminomethylated fluoropiperidines
- Protein kinase B inhibitors
- GlyT1 inhibitors
- Piperidinecarboxylic acids via nitrilase-catalyzed enantioselective synthesis
Reactant for
- Replacement in CB2 receptor inhibitors
- Double addition reactions of methyllithium and n-butyllithium to unsaturated nitriles
| [Synthesis]
The general procedure for the synthesis of N-Boc-4-cyanopiperidine from tert-butyl 4-carbamoylpiperidine-1-carboxylate is as follows: to a solution of ethyl acetate (EtOAc, 1 mL, 1 M) containing an aldoxime or amide (1.0 mmol) and triethylamine (Et3N, 1.5 mmol) was added batchwise to XtalFluor-E (1.1 mmol) at room temperature. ). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction was quenched with saturated sodium bicarbonate (NaHCO3) solution and extracted with aqueous sodium carbonate (Na2CO3) and dichloromethane (CH2Cl2, 2 × 10 mL). The combined organic layers were washed sequentially with water and brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give the crude product. If necessary, the crude product can be purified by fast column chromatography. | [References]
[1] Synthesis (Germany), 2015, vol. 47, # 23, p. 3758 - 3766
[2] Patent: WO2004/2483, 2004, A1. Location in patent: Page/Page column 21-22; 39-40
[3] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 12, p. 1503 - 1507
[4] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186
[5] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829 |
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