Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide
- Richard J. Ingham,
- Claudio Battilocchio,
- Joel M. Hawkins and
- Steven V. Ley
Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56
Graphical Abstract
Figure 1: Raspberry Pi® (RPi) computer operating in the laboratory, shown here without its protective case. U...
Figure 2: Two step approach to piperazine-2-carboxamide via hydrolysis followed by reduction. (a) Retrosynthe...
Figure 3: Heterogeneous hydration of pyrazine-2-carbonitrile with hydrous zirconia.
Figure 4: FlowIR™ profile for the reactor output after hydration of pyrazine-2-carbonitrile using hydrous zir...
Figure 5: (a) Fluidic setup for the zirconia catalysed hydration of aromatic nitrile. (b) Raspberry Pi® micro...
Figure 6: Flowchart describing the control sequence for operating and monitoring the hydration reaction. The ...
Figure 7: Profile for a 3 hour reaction simulating a long run. The absorbance shown is that at 1685 cm−1, whi...
Figure 8: Reactor setup for optimisation reactions. A multi-position valve (V2) was used for collecting sampl...
Figure 9: Representation of the control sequence for running experiments under a set of conditions. (See Supporting Information File 3 for...
Figure 10: Reduction products of piperazine-2-carboxamide.
Figure 11: (a) In-line reservoir schematic. The liquid level is measured by observation of a plastic float. (b...
Figure 12: Flow set up for the automated machine assisted synthesis of (R,S)-piperidine-2-carboxamide.
Figure 13: Control sequence for the two-step process.
Figure 14: Chart of monitored parameters over a 15 hour reaction. The output from the hydrolysis step is direc...
Camera-enabled techniques for organic synthesis
- Steven V. Ley,
- Richard J. Ingham,
- Matthew O’Brien and
- Duncan L. Browne
Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118
Graphical Abstract
Figure 1: The evolution of computer-based monitoring and control within the laboratory of the future. (a) In ...
Figure 2: A selection of the wide range of digital camera devices available, focusing on those that can be at...
Figure 3: (a) Network cameras (Linksys WVC54GC) in operation in the Innovative Technology Centre laboratory. ...
Figure 4: Remote transmission of video imagery and reaction monitoring data.
Figure 5: A camera can assist the chemist in a number of ways. Digital video recordings of reactions can be u...
Figure 6: Suzuki–Miyaura reaction performed within a microfluidic system. The product is observed by high-spe...
Figure 7: Friedel–Crafts reactions performed by using solid-acid catalysis at high pressures. A camera allowe...
Figure 8: (a) The video camera setup providing a view of the reaction within the microwave cavity; (b) a pall...
Figure 9: (a) Buchwald–Hartwig coupling within a microchannel reactor. (b) Camera view of aggregate deposits ...
Figure 10: The key diprotected piperazic acid precursor in the synthesis of chloptosin.
Figure 11: (a) Piperazic acid mixture, and (b) apparatus for enantiomeric upgrading by recorded crystallisatio...
Figure 12: (a) Crystallisation of a Mn(II) polyoxometalate. (b) A bespoke reactor produced using additive fabr...
Figure 13: Computer processing of digital imagery produces numerical data for later processing.
Figure 14: (a) The Morphologi G3 particle image analyser, which uses images captured with a camera microscope ...
Figure 15: Use of the Python Imaging Library to analyse the proportion of an image consisting of red pixels. A...
Figure 16: (a) Arduino [73,75], a flexible open-source platform for rapidly prototyping electronic applications. (b) ...
Figure 17: Patented device incorporating a standard 96-well plate illuminated by a white-light source. The pla...
Figure 18: Simple colour-change experiments to assess a new AF-2400 gas permeable flow reactor. The reactor co...
Figure 19: (a) Ozonolysis of a series of alkenes using ozone in a bottle-reactor; (b) Glaser–Hay coupling usin...
Figure 20: (a) Camera-assisted titration of ammonia using bromocresol green. NH3 is dissolved in the gas-flow ...
Figure 21: (a) Bubble-counting setup. As the output of the gas-flow reactor (hydrogen dissolved in dichloromet...
Figure 22: Usage of digital cameras to enable remote control of reactions.
Figure 23: In-line solvent switching apparatus. The reactor output is directed into a bottle positioned on a h...
Figure 24: Catch and Release apparatus. (1) The amide intermediate is sequestered onto the central sulfonic ac...
Figure 25: Clips from video footage showing the silica reagent changing appearance; the arrows indicate the ed...
Figure 26: Combination of computer vision and automation to enable machine-assisted synthetic processes.
Figure 27: A coloured float at the interface between heavy and light solvents allows a camera to recognise the...
Figure 28: Graphical demonstration of the image-recognition process. At the start of the experiment, the colou...
Figure 29: Application of the computer-vision-enabled liquid–liquid extractor. The product mixture of a hydraz...
Figure 30: Application of a computer-vision technique to measure the dispersion of a plug of material passing ...
Figure 31: Multiple extractors in series controlled by a single camera.
Figure 32: Two-step synthesis of branched aldehydes from aryl iodides using two reactive gases. A liquid–liqui...
