How could you convert N-methylbenzamide to the following compounds?
a. N-methylbenzylamine

Using any necessary reagents, show how you can accomplish the following multistep syntheses.

(b)

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide → benzylamine

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amine syntheses can be used for the following conversions.

(c) 1-bromo-3-phenylheptane → 3-phenylheptan-1-amine

Starting with cyclohexene, how can the following compounds be prepared?

b. cyclohexylmethylamine

What are the products of the following reactions?

h.

Predict the products of the following reactions:

(k)

Reductive amination of aldehydes and ketones is a versatile method for attaching alkyl groups to amines, but the alkyl group is restricted to a 1° or 2° carbon by this method. Prof. Phil Baran of Scripps Research Institute has reported (Science, 2015, 348 (6237), 886–891) a novel way to reduce an aromatic nitro group and add the resulting amine to an alkene so that the aromatic amine is bonded to a 3° carbon—all in a continuous sequence of reactions.

For example:

Predict the products using these starting materials, all of which are reported in this paper.

(c)

(d)

Predict the products of the following reactions:

(d)