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TCI Practical Example: Condensation Reaction with a Capsule Reagent containing DMT-MM
We are proud to present the condensation reaction of 4-bromobenzoic acid and morpholine using the capsule reagent. This reagent can eliminate the need for weighing. Each capsule contains 0.30 mmol of DMT-MM, a condensing agent.
Used Chemicals
Procedure
Reagents for condensation capsule (DMT-MM) (one capsule) was added to a solution of 4-bromobenzoic acid (60 mg, 0.30 mmol, 1.0 eq.), morpholine (27.4 μL, 0.315 mmol, 1.05 eq.) in methanol (1.5 mL) at room temperature. The mixture was stirred at 30 °C for 24 hours. The reaction solution was diluted with ethyl acetate (20 mL) and filtrated through Celite pad. The filtrate was washed with sat. Na2SO4 aq. (30 mL), 1 mol/L HCl aq. (10 mL), sat. NaHCO3 aq. (15 mL) and brine (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexane = 4:1 - 1:1) to afford (4-bromophenyl)(morpholino)methanone (70 mg, 86% yield) as a white solid.
Experimenter's Comments
- The reaction mixture was monitored by UPLC.
- The shape of the capsule is like below image and each capsule includes DMT-MM (ca. 0.30 mmol).
- The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose).
- Saturated sodium sulfate solution used during partitioning was used to remove HPMC.
Analytical Data
(4-Bromophenyl)(morpholino)methanone
1H NMR (400 MHz, DNSO-d6); δ 7.65 (dt, J = 8.9 Hz, 2.1 Hz, 2H), 7.37 (dt, J = 8.5 Hz, 2.1 Hz, 2H), 3.61-3.24 (brm, 8H).
Lead Reference
- Hydrophobic Pockets of HPMC Enable Extremely Short Reaction Times in Water
Other References
- HPMC: A Biomass-Based Semisynthetic Sustainable Additive Enabling Clean and Fast Chemistry in Water