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Topic: Synthesis of piperidine by Mannich Reaction  (Read 5363 times)

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Offline lutesium

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Synthesis of piperidine by Mannich Reaction
« on: February 03, 2008, 07:53:13 PM »
Dear Sir/Ma'am

Can piperidine be synthesised by Mannich Reaction??? By condensing Ammonium Acetate with 2 moles of formaldehyde and one mole of acetone and then reducing the product with LiAlH4???


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Offline movies

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Re: Synthesis of piperidine by Mannich Reaction
« Reply #1 on: February 04, 2008, 11:52:50 AM »
That won't get you to piperidine.  LiAlH4 would reduce the ketone to an alcohol, not an alkane.
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Offline lutesium

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Re: Synthesis of piperidine by Mannich Reaction
« Reply #2 on: February 04, 2008, 01:51:26 PM »
So what reactants can reduce an alcohol to a hydrocarbon??? I'm sure that Red Phosphorus + HI will do it but I'm afraid that N bridge would rupture creating hexyl amine!!!


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Offline Kryolith

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Re: Synthesis of piperidine by Mannich Reaction
« Reply #3 on: February 04, 2008, 02:03:31 PM »
You can easily reduce ketones to alkanes with the Huang-Minlon modification of the Wolff-Kishner reduction:

http://en.wikipedia.org/wiki/Wolff-Kishner_reduction
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