Piperazinone derivatives, such as compound 4, are being investigated for their potential use in the treatment of migraines as well as a variety of other diseases, including hypertension and sepsis. The following two-step synthetic procedure was developed as a general method for producing a variety of piperazinone derivatives (Tetrahedron Lett. 2009, 50, 3817-3819). Compound 1 is a readily available starting material that can be converted to compound 2 via an SN2 process. Reductive amination of compound 2 affords compound 3 which is short-lived and rapidly undergoes acid-catalyzed amide formation to the cyclic product 4a, piperazinone derivative. 1 H₂N. Br OMe NaHCO3 DMF Challenge Problem 22.100a Incorrect. OMe 2 PhCH,NH NaBH3CN 3 AcOH, heat Draw the structure of compound 3. If it is a pair of diastereomers, draw both diastereomers. Do NOT use abbreviations such as Ph or OMe when drawing the structure(s). Draw Your Solution

Piperazinone derivatives, such as compound 4, are being investigated for their potential use in the treatment of migraines as well as a variety of other diseases, including hypertension and sepsis. The following two-step synthetic procedure was developed as a general method for producing a variety of piperazinone derivatives (Tetrahedron Lett. 2009, 50, 3817-3819). Compound 1 is a readily available starting material that can be converted to compound 2 via an SN2 process. Reductive amination of compound 2 affords compound 3 which is short-lived and rapidly undergoes acid-catalyzed amide formation to the cyclic product 4a, piperazinone derivative. 1 H₂N. Br OMe NaHCO3 DMF Challenge Problem 22.100a Incorrect. OMe 2 PhCH,NH NaBH3CN 3 AcOH, heat Draw the structure of compound 3. If it is a pair of diastereomers, draw both diastereomers. Do NOT use abbreviations such as Ph or OMe when drawing the structure(s). Draw Your Solution

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.66P

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