[pyrotab]

I’m trying to synthesize something, but can’t figure out how to add a methyl group to a amine. Can anyone explain the carbon nitrogen bonds or how to get from nh2 to nhch3 thanks?

[nj_bartel]

gabriel amine synthesis, pthalimide synthesis, reducing amination, SN2 on alkyl halide, acyl chloride with amine then reduce

[StarvinMarvin]

I wouldn't be so sure about adding alkyl halide to an amine. Most likely you'd obtain tertiary amines and quaternary salts.

[pyrotab]

Yea, but what about adding this methyl group to the nitrogen of an amine

[pyrotab]

what about a reaction of hydrochloric acid with hexamine and then adding my amine and then reducing?

[StarvinMarvin]

Yea, but what about adding this methyl group to the nitrogen of an amine

That is what I referred to: If you add it like this, methyl halide will simply add once more to form tertiary amine and then once again to form a salt.

The most reliable ways of preparing (secondary) methylamine of sort R-NH-Me are:

a) acylation with acetyl chloride and reduction of the obtained amide with NaBH4 or AlLiH4.

b) Schiff condensation with acetaldehyde to form imine followed by its immediate reduction by NaBH4, NaBH3CN, NaBH(OAc)3 etc which is collectively referred to as "reductive amination".

And somebody before posted those two methods, but in my view those are most straightforward and simplest.

[pyrotab]

what about using Methyl iodide as a substrate for SN2 substitutio?

[sjb]

The most reliable ways of preparing (secondary) methylamine of sort R-NH-Me are:

a) acylation with acetyl chloride and reduction of the obtained amide with NaBH4 or AlLiH4.

b) Schiff condensation with acetaldehyde to form imine followed by its immediate reduction by NaBH4, NaBH3CN, NaBH(OAc)3 etc which is collectively referred to as "reductive amination".

And somebody before posted those two methods, but in my view those are most straightforward and simplest.

These would give RNHEt, wouldn't they?

[StarvinMarvin]

yep, I meant formaldehyde. Actually to make those kind of amines you'd need to use methylamine and corresponding aldehyde R-CHO, but I wanted just to make a point about the method and that's where the mistake came from.

[pyrotab]

Im going to be smart as this  guy ^^^^^^^^one day

[nj_bartel]

what about using Methyl iodide as a substrate for SN2 substitutio?

As the smart guy with glasses said before ( ), if you try to SN2 to make a primary/secondary/tertiary amine, you're very likely going to get a large mixture of products because the amine, once substituted, retains most of its nucleophility, and in the case of primary -> secondary, increases nucleophilicity.