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| | TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Basic information | | Uses |
| Product Name: | TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE | | Synonyms: | 1-Piperidinecarboxylic acid, 4-(aminocarbonyl)-, 1,1-dimethylethyl ester;1-N-BOC-ISONIPECOTAMIDE;1-Boc-4-Piperidinecarboxamide;tert-Butyl 4-(aminocarbonyl)tetrahydropyridine-1-carboxylate;N-BOC-piperidine-4-carboxamide;tert-butyl 4-carbaMoylpiperidine-1-carboxylate;4-Carbamoylpiperidine, N1-BOC protected;tert-Butyl 4-carbamoylpiperidine-1-carboxylate, 1-(tert-Butoxycarbonyl)-4-carbamoylpiperidine, 1-(tert-Butoxycarbonyl)piperidine-4-carboxamide | | CAS: | 91419-48-6 | | MF: | C11H20N2O3 | | MW: | 228.29 | | EINECS: | 000-000-0 | | Product Categories: | 91419-48-6 | | Mol File: | 91419-48-6.mol |  |
| | TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Chemical Properties |
| Melting point | 158-160 | | Boiling point | 384.4±31.0 °C(Predicted) | | density | 1.123±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | powder to crystal | | pka | 16.40±0.20(Predicted) | | color | White to Almost white | | InChI | InChI=1S/C11H20N2O3/c1-11(2,3)16-10(15)13-6-4-8(5-7-13)9(12)14/h8H,4-7H2,1-3H3,(H2,12,14) | | InChIKey | YHFUWPUJUMZXBD-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC(C(N)=O)CC1 |
| Hazard Codes | Xi | | Hazard Note | Irritant | | HS Code | 29333990 |
| | TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Usage And Synthesis |
| Uses | 1-BOC-piperidine-4-carboxamide is a common organic synthon in which the Boc group can be removed under acidic conditions, releasing the cyclohexylamine structure. Furthermore, the formamide structure on the ring can be converted to a cyano group under certain reaction conditions; and the oxygen atom on the formamide can be converted to a sulfur atom by the action of Lawesson reagent. | | Chemical Properties | White powder | | Synthesis | General procedure for the synthesis of tert-butyl 4-carbamoylpiperidine-1-carboxylate from 1-Boc-4-piperidinecarboxylic acid: a mixture of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (220 mg, 2.88 mmol), ammonium chloride (154 mg, 2.88 mmol), EDCI (367 mg, 1.92 mmol) and HOAT (195 mg. 1.44 mmol) were dissolved in dichloromethane (10 mL) at 0 °C, followed by dropwise addition of DIPEA (1.0 mL, 5.77 mmol). After dropwise addition, the reaction mixture was stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was washed with distilled water (10 mL x 3). The organic layer was separated and dried with anhydrous Na2SO4 and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to afford tert-butyl 4-carbamoylpiperidine-1-carboxylate as a white solid (160 mg, 73% yield).1H NMR (400 MHz, CD3OD): δ 4.11 (d, J = 13.4 Hz, 2H), 2.76-2.86 (m, 2H), 2.38-2.45 ( m, 1H), 1.79 (d, J = 11.2 Hz, 2H), 1.52-1.62 (m, 2H), 1.47 (s, 9H).MS-ESI: m/z 173.20 [M-55]+. | | References | [1] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00539
[2] Patent: CN105399698, 2016, A. Location in patent: Paragraph 1621-1623
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9196 - 9213
[4] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 114
[5] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186 |
| | TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Preparation Products And Raw materials |
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