--- title: "Gabriel synthesis Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/gabriel-synthesis/ description: "Gabriel synthesis template: Phthalimide is deprotonated and alkylated with benzyl bromide; hydrazine then releases benzylamine. Preview it, then open and…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Gabriel synthesis [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Gabriel synthesis template ![Gabriel synthesis template: Phthalimide is deprotonated and alkylated with benzyl bromide; hydrazine then releases benzylamine.](https://www.moldraw.com/templates/gabriel-synthesis.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). Phthalimide is deprotonated and alkylated with benzyl bromide; hydrazine then releases benzylamine. ## Mechanism step by step Phthalimide as a protected NH₂: primary amines without over-alkylation 1. **Deprotonation** – The N–H between two C=O is acidic (pKa 8.3) 2. **N-Alkylation (SN2)** – The imide anion displaces bromide 3. **Hydrazine attacks** – First of two addition–elimination steps (Ing–Manske) ## Key points - The N-alkyl phthalimide is no longer nucleophilic: only one alkyl group adds. - Hydrazine attacks both C=O groups in turn, releasing the amine and phthalhydrazide. - Acid or base hydrolysis also works but needs harsher conditions. - Only for primary alkyl halides (SN2); aryl halides do not react. Drawn with 122 atoms, 10 arrows, 5 shapes – every one editable in MolDraw. ## Sources - [Gabriel, Ber. Dtsch. Chem. Ges. 1887, 20, 2224](https://doi.org/10.1002/cber.18870200227) Original paper - [Ing & Manske, J. Chem. Soc. 1926, 2348](https://doi.org/10.1039/JR9260002348) Original paper - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012](https://openlibrary.org/isbn/9780199270293) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Gabriel synthesis template free? You can preview the Gabriel synthesis template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Gabriel synthesis template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### Which name reactions are included? 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