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CAS No. : | 14473-91-7 | MDL No. : | MFCD00004382 |
Formula : | C9H7BrO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YEMUSDCFQUBPAL-SNAWJCMRSA-N |
M.W : | 227.05 | Pubchem ID : | 776461 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N-methyl-acetamide; water; | REFERENCE EXAMPLE 49 To 3-bromocinnamic acid (2.0 g) were added thionyl chloride (25 ml) and dimethylformamide (catalytic amount), and the mixture was refluxed for 1.5 hours. The solvent was evaporated, and the residue was dissolved in tetrahydrofuran. The mixture was dropwise added to a suspension of <strong>[29608-05-7]1-(4-aminobenzyl)piperidine</strong> (1.7 g) and diisopropylethylamine (4 ml) in tetrahydrofuran (5 ml) under ice-cooling. Under nitrogen atmosphere, the mixture was stirred at room temperature over night. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 1-(4-(3-bromocinnamoylamino)benzyl)piperidine (1.8 g) as colorless crystals. mp 144-145 C.; 1 H-NMR(delta ppm, CDCl3): 1.37-1.49 (2H, m), 1.52-1.63 (4H, m), 2.34-2.39 (4H, m), 3.45 (2H, s), 6.54 (1H, d, J=15.5 Hz), 7.21-7.33 (3H, m), 7.41-7.57 (5H, m), 7.67 (1H, d, J=15.5 Hz), 7.69 (1H, s). IR(KBr) nu: 3270, 2934, 1663 cm31 1. Anal. for C21 H23 BrN2 O.0.2H2 O: Calcd. C,62.60; H,5.85; N,6.95. Found C,62.67; H,5.79; N,6.93. |
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