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Magazine Chapter 19: Q26P (page 1018)
Show how to synthesize the following amines from the indicated starting materials by reductive amination.
(a) benzylmethylamine from benzaldehyde
(b) N-benzylpiperidine from piperdine
(c) N-cyclohexylaniline from cyclohexanone
(d) cyclohexylamine from cyclohexanone
(e)
(f)
Short Answer
(a)
(b)
(c)
(d)
(e)
(f)
Step by step solution
Reductive amination
The most useful method for synthesis of amines is the reductive amination. In this process, 10 or 20 alkyl group is added to the nitrogen atom. Generally, aldehyde is used to add 10 alkyl group and ketone is used to add 20 alkyl group.
Synthetic methodology
a.
Benzalhedyde combines with methylamine (a primary amine) to undergo a condensation process to form (E)-N-benzylidenemethanamine (a Schiff base) which on further reduction with LiAlH4 (lithium aluminum hydride) gives N-methyl-1-phenylmethanamine ( a secondary amine).
reaction a
b.
Benzalhedyde combines with piperidine (a secondary amine) to undergo a condensation process to form an iminium salt (1-benzylidenepiperidin-1-ium) which on further reduction with NaBH(OAc)3 (sodium triacetoxy borohydride)gives 1-benzylpiperidine ( a tertiary amine).
reaction b
c.
Cylohexanone combines with aniline (a primary amine) to undergo a condensation process to form N-cyclohexylideneaniline (a Schiff base) which on further reduction with LiAlH4 (lithium aluminum hydride) gives N-cyclohexylaniline ( a secondary amine).
reaction c
d.
Cylohexanone combines with hydroxylamine (zero alkyl groups) to undergo a condensation process to form cyclohexanone oxime which on further reduction with LiAlH4 (lithium aluminum hydride) gives cyclohexanamine ( a primary amine).
reaction d
e.
1-phenylpropan-2one combines with hydroxylamine (zero alkyl groups) to undergo a condensation process to form (Z)-1-phenylpropan-2-one oxime which on further reduction with LiAlH4 (lithium aluminum hydride) gives 卤amphetamine or 1-phenylpropan-2-amine ( a primary amine).
reaction e
f.
Cyclopenatnone combines with piperidine (a secondary amine) to undergo a condensation process to form an iminium salt (1-cyclopentylidenepiperidin-1-ium) which on further reduction with NaBH(OAc)3 (sodium triacetoxy borohydride)gives 1-cyclopentylpiperidine ( a tertiary amine).
reaction f
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