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O CH 3
H
O
H O
H
H
HOCH3
H
N N H
O CH3
OH OH
H
H
H
N
N H Na
H B CN N
OH 2
H H
H
H
Neutralization
O CH3
step, NaOH
H
N
NH
When
ketone
or
aldehydes
react
with
1°
amines
an
imine
is
formed.
Enamines
are
the
product
of
2°
amines
and
an
aldehyde
or
a
ketone.
These
imines
or
enamines
can
be
reduced
to
2°
or
3°
amines,
respectively.
One
way
is
hydrogen
addition
using
a
metal
catalyst.
The
mechanism
for
the
use
of
a
non-‐metal-‐hydride
as
the
reducing
agent
is
shown
above.
This
synthesis
procedure
requires
the
formation
of
an
intermediate
imine.
Because
the
formation
of
an
amine
from
the
imine
does
not
require
a
nucleophilic
attack
of
the
nitrogen
there
is
no
concern
with
over-‐alkylation.
The
reaction
between
an
amine
and
formaldehyde
followed
by
reductive
amination
can
produce
a
selectively
methylated
amine.
A
tertiary
amine
is
usually
the
product
of
the
reaction
if
excess
formaldehyde
is
used.
The
mechanism
for
the
synthesis
is
the
same
as
the
above.
CH3
O
NH2 1) H H
(xs) / NaBH3CN, acetic acid
N
CH3CN / H2Osolvent system CH3
2) neutralization, NaOH