N,N-diethylcathinone (diethylpropion) [CAS 90-84-6, 39648-49-2, 39648-50-5; InChIKey XXEPPPIWZFICOJ-

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Date

26 reactions in Reaxys

2016-02-22 07h:34m:29s (EST)

O

1. Query

N

Search as: As drawn

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O

O N H

Br

N

Rx-ID: 2958744 View in Reaxys 1/26 Yield

Conditions & References

85 %

With N-ethyl-N,N-diisopropylamine, sodium iodide in acetonitrile, Time= 16h, T= 40 °C Mulvihill, Mark J.; Cesario, Cara; Smith, Vanessa; Beck, Patricia; Nigro, Anthony; Journal of Organic Chemistry; vol. 69; nb. 15; (2004); p. 5124 - 5127 View in Reaxys

60 %

in toluene, Time= 72h Welle, Frank; Verevkin, Sergej P.; Keller, Manfred; Beckhaus, Hans-Dieter; Ruechardt, Christoph; Chemische Berichte; vol. 127; nb. 4; (1994); p. 697 - 710 View in Reaxys With potassium carbonate in benzene Mueller,H.K.; Mueller,E.; Justus Liebigs Annalen der Chemie; vol. 689; (1965); p. 134 - 140 View in Reaxys in benzene, Ambient temperature Cattaneo,A. et al.; Farmaco, Edizione Scientifica; vol. 17; (1962); p. 308 - 319 View in Reaxys

O

O

N H

N

Rx-ID: 36720828 View in Reaxys 2/26 Yield 80 %

Conditions & References Stage 1: With 1,10-phenanthroline, copper(ll) bromide in dimethyl sulfoxide, Time= 0.166667h, T= 20 °C Stage 2: With oxygen in dimethyl sulfoxide, Time= 1.5h, T= 35 °C , p= 760.051Torr , Sealed tube Evans, Ryan W.; Zbieg, Jason R.; Zhu, Shaolin; Li, Wei; Macmillan, David W. C.; Journal of the American Chemical Society; vol. 135; nb. 43; (2013); p. 16074 - 16077 View in Reaxys

72 %

With Na2CO3*1.5H2O2, NH4I in acetonitrile, Time= 24h, T= 50 °C Jiang, Qing; Xu, Bin; Zhao, An; Jia, Jing; Liu, Tian; Guo, Cancheng; Journal of Organic Chemistry; vol. 79; nb.

18; (2014); p. 8750 - 8756 View in Reaxys

O

HO

N H

N

Rx-ID: 39395155 View in Reaxys 3/26 Yield 60 %

Conditions & References Stage 1: With N-bromosuccinmide in 1,4-dioxane Stage 2: in 1,4-dioxane, Time= 24h, T= 20 °C Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb. 3; (2015); p. 406 - 409 View in Reaxys

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O

OH

O

H

H

O

HO

O

O

HO

O

O

O

O

O N

N

O O O O

OH

Rx-ID: 40856746 View in Reaxys 4/26 Yield

Conditions & References

85 %

With sodium hydroxide in water, acetone, T= 20 °C Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O

O

O

OH

HO

O

O

N

O

H

H

O

O N

O O O O

O

OH

OH O

Rx-ID: 40856749 View in Reaxys 5/26 Yield

Conditions & References

78 %

With sodium hydroxide in water, acetone, T= 20 °C Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O Cl

N H

H

O N

Br

Rx-ID: 40856770 View in Reaxys 6/26 Yield

Conditions & References

62 %

With triethylamine in dichloromethane, Time= 21h, T= 20 °C Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O N H

N

Rx-ID: 41729693 View in Reaxys 7/26 Yield

Conditions & References

62 %

Stage 1: With N-Bromosuccinimide, water, Time= 1.2h, T= 80 °C , Inert atmosphere Stage 2: in acetone, T= 20 °C , Inert atmosphere Shinde, Mahesh H.; Kshirsagar, Umesh A.; Organic and Biomolecular Chemistry; vol. 14; nb. 3; (2016); p. 858 - 861 View in Reaxys

N

O Si O

N

Rx-ID: 38105675 View in Reaxys 8/26

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Yield

Conditions & References

62 %

With [bis(acetoxy)iodo]benzene in dichloromethane, T= 25 °C , Inert atmosphere, Schlenk technique Mizar, Pushpak; Wirth, Thomas; Angewandte Chemie - International Edition; vol. 53; nb. 23; (2014); p. 5993 - 5997; Angew. Chem.; vol. 126; nb. 23; (2014); p. 6103 - 6107,5 View in Reaxys

HO

O

H

O

O

H

O

HO

O O

N

O

O

O N

O O O

O

O

OH

OH

Rx-ID: 40856752 View in Reaxys 9/26 Yield 24 %

Conditions & References With sodium hydroxide in water, acetone, T= 20 °C Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O Br

N

Rx-ID: 39395171 View in Reaxys 10/26 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / |Inert atmosphere 1.2: 0 °C / |Inert atmosphere 2.1: N-bromosuccinmide / 1,4-dioxane 2.2: 24 h / 20 °C With N-bromosuccinmide, iodine, magnesium in tetrahydrofuran, 1,4-dioxane, 1.1: |Grignard Reaction Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb. 3; (2015); p. 406 - 409 View in Reaxys

O

O N

Br

Rx-ID: 40856768 View in Reaxys 11/26 Yield

Conditions & References Reaction Steps: 3 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C 3: sodium hydroxide / water With triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys Reaction Steps: 3 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C 3: sodium hydroxide / water With triethylamine, sodium hydroxide in dichloromethane, water, acetone

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys Reaction Steps: 3 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C 3: sodium hydroxide / water With triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O

O

N

Rx-ID: 40856787 View in Reaxys 12/26 Yield

Conditions & References Reaction Steps: 4 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C 4: sodium hydroxide / water With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys Reaction Steps: 4 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C 4: sodium hydroxide / water With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys Reaction Steps: 4 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C 4: sodium hydroxide / water With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O

O N

N

Rx-ID: 40856791 View in Reaxys 13/26 Yield

Conditions & References Reaction Steps: 2

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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1: sodium hydroxide / acetone; water / 20 °C 2: sodium hydroxide / water With sodium hydroxide in water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys Reaction Steps: 2 1: sodium hydroxide / acetone; water / 20 °C 2: sodium hydroxide / water With sodium hydroxide in water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

N

O O O O

OH

Rx-ID: 40856757 View in Reaxys 14/26 Yield

Conditions & References With sodium hydroxide in water Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O

HO

O

O

O N

Br

O O O O

OH

Rx-ID: 40856761 View in Reaxys 15/26 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C With triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O Br

HO

O

O

O N

O O O O

OH

Rx-ID: 40856762 View in Reaxys 16/26 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C With triethylamine, sodium hydroxide in dichloromethane, water, acetone

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

Br

O O O O

OH

Rx-ID: 40856763 View in Reaxys 17/26 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / dichloromethane / 21 h / 20 °C 2: sodium hydroxide / acetone; water / 20 °C With triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

N

O O O O

OH

Rx-ID: 40856772 View in Reaxys 18/26 Yield

Conditions & References With sodium hydroxide in water Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

N

O O O O

OH

Rx-ID: 40856773 View in Reaxys 19/26 Yield

Conditions & References With sodium hydroxide in water Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO O

O

O

O N

O O O O

OH

Rx-ID: 40856780 View in Reaxys 20/26 Yield

Conditions & References Reaction Steps: 3 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2016-02-22 07:45:06

With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

O O O O

OH

Rx-ID: 40856781 View in Reaxys 21/26 Yield

Conditions & References Reaction Steps: 3 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

HO

O

O

O

O N

O O O O

OH

Rx-ID: 40856782 View in Reaxys 22/26 Yield

Conditions & References Reaction Steps: 3 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C 3: sodium hydroxide / acetone; water / 20 °C With bromine, acetic acid, triethylamine, sodium hydroxide in dichloromethane, water, acetone Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O

O

N

Rx-ID: 40856790 View in Reaxys 23/26 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; bromine / 22 h / 20 °C 2: triethylamine / dichloromethane / 21 h / 20 °C With bromine, acetic acid, triethylamine in dichloromethane Zhou; Bouazzaoui; Jones; Goodrich; Bell; Sheldrake; Horton; Coles; Fletcher; Organic and Biomolecular Chemistry; vol. 13; nb. 37; (2015); p. 9629 - 9636 View in Reaxys

O N H

(+-)-1-acetoxy-1-phenyl-acetone

N

Rx-ID: 7789910 View in Reaxys 24/26

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Yield

Conditions & References With methanol, T= 180 °C Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; ; (1955); p. 8175 View in Reaxys

O

1.) MoO2Cl2+(CH3)3Al-complex

N

O N

N

Rx-ID: 7434088 View in Reaxys 25/26 Yield

Conditions & References With N,N,N',N',N'',N''-hexamethylphosphoric triamide, 1.) THF, -70 deg C - -60 deg C, 15 min, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Enk, Manfred; Fiegenbaum, Petra; Hansmersmann, Ursula; Kaschube, Wilfried; et al.; Chemische Berichte; vol. 127; nb. 1; (1994); p. 127 - 136 View in Reaxys

O N

Rx-ID: 7789909 View in Reaxys 26/26 Yield

Conditions & References /BRN= 2830645/ Hyde; Browning; Adams; Journal of the American Chemical Society; vol. 50; (1928); p. 2290 View in Reaxys Entspr. Aminoketon, CH3I Sekiya; Kawarabata; Chemical and Pharmaceutical Bulletin; vol. 18; (1970); p. 2081,2085 View in Reaxys α-Brom-propiophenon, Diaethylamin (100grad) Patent; Temmler Werke; US3001910; ; vol. 56; nb. 2384; (1962) View in Reaxys Propiophenon, Brom, 1.2-Dichlor-aethan, 35grad 1)Diaethylamin, Bzl. 75grad Dychanow; Korotkina; Meditsinskaya Promyshlennost SSSR; vol. 15; nb. 6; (1961); p. 22,23; ; nb. 27043; (1961) View in Reaxys PhCOEt 1)Br2 2)Et2NH Patent; Temmler-Werke; GB945162; (1963); ; vol. 60; nb. 15784; (1964) View in Reaxys The anorectics which could be used in the present invention include the following: ... chlorophentermine fenfluramine benzphetamine phenmetrazine diethylpropion phenylpropanolomine Patent; Cooper; Irving; US4255439; (1981); (A1) English View in Reaxys

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