[Who_ate_my_cat]

Can anyone help with this problem. I'm familiar with how to convert most alcohols to an amine but this question has me stuck and I feel like I'm missing something obvious. The question states: "How would you prepare propylamine from 1-butanol" and states there are two methods. I don't see how you would shorten the butanol and then add an NH2 to the end.

Any hints or steps would be appreciated.

[sjb]

What are your thoughts? What reactions of primary alcohols do you know? How can you make amines?

[Who_ate_my_cat]

Well, I've found a lot of "dead-ends" thus far.

I know you can make amines using Hofmann and Curtius rearrangement. (using CH3I and NaN3). There's also reduction using NaBH4 or LiAlH4 and THF. There's the Gabriel Reaction and also reductive amination from Aldehydes or Ketones. But I can't find anything that will directly convert the butanol to propylamine. My thinking is to convert the alcohol to a ketone or Aldehyde using PCC and then cleaving off the end and replacing with an NH2 somehow. I'm still working on that though.

[sjb]

I'm not seeing in your question where it has to be one step, but you have some good ideas.

[wildfyr]

What reactions can break a carbon-carbon bond? This could be alkyl, alkene, or alkyne, but you should go from one molecule to two. I don't see how this could be done in one step. Maybe if you're really clever it could be done in one (difficult) pot.

Also, I'm just curious but does undergrad ochem teach the Staudinger reduction? It's azide to amine using triphenylphosphine