Published TCIMAIL newest issue No.197
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TCI Practical Example: The Condensation Reaction Using a Capsule Reagent
We are proud to present the condensation reaction of 4-bromobenzoic acid and morpholine using the capsule reagent. This reagent can omit weighing the condensing agents. 0.25 mmol of EDCI·HCl and 0.04 mmol of HOBt·H2O are encapsulated in each capsule.
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Used Chemicals
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Procedure
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Reagents for condensation reactions (HPMC encapsulated) (one capsule) was added to a solution of 4-bromobenzoic acid (40 mg, 0.20 mmol, 1.0 eq.), morpholine (17 μL, 0.20 mmol, 1.0 eq.) in water (1 mL) at room temperature and the mixture was stirred at 30 °C for 24 hours. The reaction solution was diluted with sat. Na2SO4 aq. (15 mL) and extracted with ethyl acetate (15 mL x 2), and the organic layer was washed with 2 mol/L HCl aq. (15 mL), sat. NaHCO3 aq. (15 mL) and brine (15 mL). The organic layer was dried over sodium sulfate, concentrated under reduced pressure, and the crude product was purified by silica gel chromatography (hexane:ethyl acetate = 2:1 - 1:1) to afford (4-bromophenyl)(morpholino)methanone (48 mg, 89% yield) as a white solid.
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Experimenter’s Comments
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The reaction mixture was monitored by UPLC.
The shape of the capsule is like below image and each capsule includes EDCI·HCl (ca. 0.25 mmol) and HOBt·H2O (ca. 0.04 mmol).
The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose).
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Analytical Data
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(4-Bromophenyl)(morpholino)methanone
1H NMR (400 MHz, CDCl3); δ 7.57 (d, J = 8.4 Hz, 2H), 7.30 (d, J = 8.4 Hz, 2H), 3.74-3.44 (m, 8H).
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Lead Reference
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- Hydrophobic Pockets of HPMC Enable Extremely Short Reaction Times in Water
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Other References
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- HPMC: A Biomass-Based Semisynthetic Sustainable Additive Enabling Clean and Fast Chemistry in Water