[bcoots]

I would like to make an N-alkyl Morpholine. There is a literature method that uses N-alkyl amine plus dichloroethyl ether.

I would like to avoid using this chlorinated raw material, and wondered if an N-alkyl diethanolamine could be dehydrated to give the morpholine ring.

Any ideas?

[Arkcon]

Your plan seems to match the one given in Wikipedia:  http://en.wikipedia.org/wiki/Morpholine#Production And there is also a reference given there if it helps you understand how its done even better.

[Dan]

What is R?

I would consider reductive amination of carbonyls with morpholine - but it depends on what R is.

[bcoots]

Dan - R is an alkyl group derived from a C18 fatty acid.

[Dan]

Then I would probably do one of two things:

1. Make the corresponding "fatty acid aldehyde" and reductively aminate it with morpholine or...
2. Couple the fatty acid with morpholine and reduce the resulting amide to the amine.

The second option is probably the easier one.