9,10-didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide (LSD) [CAS 50-37-3; InChIKey VAYOS

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12 reactions in Reaxys

2016-03-05 01h:20m:29s (EST)

O

1. Query

N HN

N H

Search as: As drawn

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2016-03-05 01:26:58

O

O

O H

N

HN

N

HN

N

HN

N

N H

H

H

N

Rx-ID: 2986424 View in Reaxys 1/12 Yield

Conditions & References

10 %, 75 % With hydrogen, platinum in ethyl acetate, Time= 2h, p= 760Torr , Ambient temperature Ishii, Hisashi; Niwaguchi, Tetsukichi; Nakahara, Yuji; Hayashi, Makoto; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 902 - 905 View in Reaxys 75 %, 10 % With hydrogen, platinum in ethyl acetate, Time= 2h, p= 760Torr , Ambient temperature Ishii, Hisashi; Niwaguchi, Tetsukichi; Nakahara, Yuji; Hayashi, Makoto; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 902 - 905 View in Reaxys

N N H

N

O

O

O N

OH

HN

N

HN

N

N

N

H

H

Rx-ID: 24058092 View in Reaxys 2/12 Yield

Conditions & References

9.0 g (75%) 1 : Synthesis of D-lysergic Acid Diethylamide (I) Example 1 Synthesis of D-lysergic Acid Diethylamide (I) A mixture of 10.0 g (0.037 mol) of d-lysergic acid in 500 ml of dry dimethyl formamide (DMF), under argon, was treated with 9.0 g of carbonyl diimidazole and stirred at room temperature for 1 hour The reaction was then treated with 38 ml of diethylamine and stirred at room temperature overnight.

The reaction was concentrated under reduced pressure.

The residue was taken up in 500 ml of methylene chloride and washed with 500 ml of water.

Insoluble material was removed by filtration and the layers were separated.

The organic portion was washed with 250 ml of saturated brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The residue was chromatographed on 800 g of silica gel using 3percent methanol in methylene chloride to yield 9.0 g (75percent) of d-lysergic acid diethylamide (LSD) as a light brown amorphous solid after evaporation of the solvents. in methanol, dichloromethane, water, N,N-dimethyl-formamide Patent; Ghoshal, Mitali; Vitone, Stephen; Sigler, Gerald F.; McNally, Alan J.; US2001/44118; (2001); (A1) English View in Reaxys

O HN

Br

O N

H

N

HN

N 3H

H

N

Rx-ID: 9014521 View in Reaxys 3/12 Yield

Conditions & References With NaBT4, Ph(PPh3)4 in N,N-dimethyl-formamide, Time= 0.5h, T= 70 °C Nagasaki, Tohru; Sakai, Katsunori; Segawa, Masaharu; Katsuyama, Yoshihiko; Haga, Nobuhiro; Koike, Masahiro; Kawada, Kenji; Takechi, Shozo; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 14; (2001); p. 993 - 1004 View in Reaxys

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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2016-03-05 01:26:58

N H

HO

N

O

O

O

H O

N H

N

OH

HN

N

HN

N

N

N

H

H

Rx-ID: 24346044 View in Reaxys 4/12 Yield

Conditions & References

3.65 g (75.7%)

1 : Synthesis of D-lysergic acid diethyl amide 1 Example 1 Synthesis of D-lysergic acid diethyl amide 1 A mixture of 4.0 g (0.015 mol) of D-lysergic acid and 200 mL of dry DMF, under argon, was treated with 3.6 g (0.022 mol) of carbonyl diimidazole and stirred at room temperature for 1 hour.

The reaction was treated with 15.2 mL (0.15 mol) of diethylamine and stirred at room temperature overnight.

The reaction was concentrated at reduced pressure.

The residue was taken up in 250 mL of CH2 Cl2 and washed with 250 mL of H2 O. Insoluble material was removed by filtration and the layers were separated.

The organic portion was washed with 250 mL of saturated brine solution, dried over anhydrous Na2 SO4 and concentrated at reduced pressure.

The residue was chromatographed on 500 g of silica gel using 3percent CH3 OH in CH2 Cl2 as eluent to yield 3.65 g (75.7percent) of D-LSD [α]D =+50.4° (c=1percent; CHCl3) as a light brown amorphous solid.

The 8α-epimer (also known as iso-LSD) has [α]D =+226° (c=1percent; CHCl3). in dichloromethane, N,N-dimethyl-formamide Patent; Roche Diagnostics Corporation; US6063908; (2000); (A1) English View in Reaxys

O

potassium-salt of/the/ (+)-lysergic acid

O N

HN

N

HN

N

N

H

H

Rx-ID: 5717693 View in Reaxys 5/12 Yield

Conditions & References With hexane, sulfur trioxide, acetonitrile, und Behandeln des Reaktionsgemisches mit Diaethylamin Patent; E.Lilly and Co.; US2736728; (1954) View in Reaxys Patent; E.Lilly and Co.; US2774763; (1955) View in Reaxys

O

O OH

HN

N

HN

N H

O N

HN

N

N

H

H

Rx-ID: 827337 View in Reaxys 6/12 Yield

Conditions & References With acetonitrile, trifluoroacetic anhydride, und Behandeln des Reaktionsgemisches mit Diaethylamin Patent; E.Lilly and Co.; US2736728; (1954) View in Reaxys Patent; E.Lilly and Co.; US2774763; (1955) View in Reaxys

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.

3/5

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O

O N H

HN

NH 2

O N

HN

N

N

HN

N

H

N

H

H

Rx-ID: 832418 View in Reaxys 7/12 Yield

Conditions & References With hydrogenchloride, sodium nitrite, und Behandeln des erhaltenen Azids mit Diaethylamin in Aether Stoll; Hofmann; Helvetica Chimica Acta; vol. 26; (1943); p. 944,947; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 251; (1938); p. 155,160 View in Reaxys

O O N

HN

N

HN N

H

N H

N

Rx-ID: 17789356 View in Reaxys 8/12 Yield

Conditions & References Reaction Steps: 2 1: aq. AcOH, AcONa, Zn / 4.5 h / 130 °C 2: 1 h With sodium acetate, acetic acid, zinc Stachulski, Andrew V.; Nichols, David E.; Scheinmann, Feodor; Journal of Chemical Research - Part S; nb. 1; (1996); p. 30 - 31 View in Reaxys

F O

O

F

O

O

O

F

F O

OH

HN

N

HN

N

HN

F F

N

N

H

N

H

H

Rx-ID: 827330 View in Reaxys 9/12 Yield

Conditions & References With acetonitrile, und Behandeln des Reaktionsgemisches mit Diaethylamin Patent; E.Lilly and Co.; US2736728; (1954) View in Reaxys Patent; E.Lilly and Co.; US2774763; (1955) View in Reaxys

O

O

I N

HN

N

HN

N H H

N H

Rx-ID: 4503705 View in Reaxys 10/12 Yield

Conditions & References Time= 1h Stachulski, Andrew V.; Nichols, David E.; Scheinmann, Feodor; Journal of Chemical Research - Part S; nb. 1; (1996); p. 30 - 31 View in Reaxys

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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O N

HN N H

Rx-ID: 5717692 View in Reaxys 11/12 Yield

Conditions & References Herstellung von (+)-Lysergsaeure-<di-<1-14 C>aethyl-amid> Stoll et al.; ; (1958); p. 405 View in Reaxys Stoll et al.; Helvetica Chimica Acta; vol. 37; (1954); p. 820,823 View in Reaxys Nakahara; Niwaguchi; Yakugaku Zasshi; vol. 94; (1974); p. 407,411; ; vol. 81; nb. 91772; (1974) View in Reaxys Niwaguchi et al.; Yakugaku Zasshi; vol. 96; (1976); p. 673,674,677 View in Reaxys Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341 View in Reaxys

O

O

OH OH HN

HO OH

O

N N H

Rx-ID: 8387476 View in Reaxys 12/12 Yield

Conditions & References Patent; Soc. Farm. Italia; FR1338023; (1961); ; vol. 60; nb. 3026f; (1964) View in Reaxys

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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