| Identification | Back Directory | [Name]
2-bromo-1-(1-Boc-piperidin-4-yl)ethanone | [CAS]
301221-79-4 | [Synonyms]
tert-Butyl 4-(2-bromoacetyl)
1-Boc-4-(2-broMo-acetyl)-piperidine
2-bromo-1-(1-Boc-piperidin-4-yl)ethanone
4-BroMoacetyl-1-(t-butoxycarbonyl)piperidine
tert-Butyl 4-(bromoacetyl)piperidine-1-carboxylate
4-(2-BroMo-acetyl)-piperidine-1-carboxylic acid tert-butyl ester
4-(2-Bromoacetyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester
1-Piperidinecarboxylic acid, 4-(2-bromoacetyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C12H20BrNO3 | [MDL Number]
MFCD11975555 | [MOL File]
301221-79-4.mol | [Molecular Weight]
306.196 |
| Chemical Properties | Back Directory | [Boiling point ]
368℃ | [density ]
1.336 | [Fp ]
176℃ | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
-2.47±0.40(Predicted) | [Appearance]
Off-white to yellow Solid | [InChI]
InChI=1S/C12H20BrNO3/c1-12(2,3)17-11(16)14-6-4-9(5-7-14)10(15)8-13/h9H,4-8H2,1-3H3 | [InChIKey]
HYRSGTXIVIMOOX-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC(C(CBr)=O)CC1 |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of N-Boc-4-(bromoacetyl)piperidine from 1-N-BOC-4-acetylpiperidine was as follows: to a suspension of tert-butyl 4-ethylpiperidine-1-carboxylate (Intermediate B5; 2.87 g, 12.6 mmol) in THF (30 mL) cooled to -78 °C, a THF solution of 1 M bis(trimethylmethylsilyl)lithium amide was slowly added (13.3 mL), and the addition time was controlled within 20 min. The reaction mixture was stirred at -78 °C for 1 h. Trimethylsilyl chloride (1.74 mL, 13.7 mmol) was added. Stirring was continued at 0 °C for 30 min, after which the reaction solution was cooled again to -78 °C and bromine (0.645 mL, 12.6 mmol) was added slowly. After the reaction mixture was naturally warmed to room temperature, the reaction was quenched by pouring into a mixture of 10% Na2S2O3 solution (20 mL) and saturated NH4Cl solution (20 mL). The organic phase was extracted with EtOAc (2×80 mL) and the organic layers were combined, which were treated to afford the target product N-Boc-4-(bromoacetyl)piperidine in a yield of 3.69 g in 96%. | [References]
[1] Patent: WO2009/150144, 2009, A1. Location in patent: Page/Page column 139
[2] Tetrahedron Letters, 2012, vol. 53, # 7, p. 852 - 853
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3419 - 3424
[4] Patent: WO2004/41279, 2004, A1. Location in patent: Page/Page column 70
[5] Patent: WO2015/88565, 2015, A1. Location in patent: Paragraph 00214 |
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