It contains about amines content which useful to II SEM B.PHARM & I PHARM D STUDENTS and dealing other organic chemistry profession ,life science students

1. ALIPAHTIC AMINES
• Unit-VI &POC I
• II SEM B.PHARM
• Aliphatic amines part I
• 06.07.2020

2. CONTENTS

3. Definition
• Amines are derivatives
Of ammonia in which one or
more hydrogen atoms have
been replaced by alkyl or aryl
groups
N
H
H
H
Ammonia
N
H
H
CH
3
N
CH
H
CH
3
3
N
CH
CH
CH
3
3
3
Methyl
amine
dimethyl
amine
trimethyl
amine

4. Classification
of amines
• Primary amine:NH2(amino
group)-A amine has only one
alkyl group directly attached to
the nitrogen
• Secondary amine: NH (imino
group)- A amine has two alkyl
group directly attached to the
nitrogen atom.
• Tertiary amine: N(Tertiary
nitrogen)-A amine has three
alkyl group directly attached to
the nitrogen atom
R NH
2
Primary amine
CH NH
3 2 C H NH
2 5 2 C H NH
6 5 2
methyl
amine
ethyl
amine
aniline
Secondary amine
C H
6 5
NH
R
R NH
CH
HC
3
3
HN
C H
2 5
C H
2 5
HN
C H
6 5
dimethyl
amine
diethyl
amine
diphenyl
amine
3
NCH
3
CH
3
CH
N
R
R R
N
C H
2 5
C H
2 5
C H
2 5
C H
6 5
N
C H
6 5
diphenyl
amine
C H
6 5
Tertiary amines

5. NH OH
4
N
R
R
R
R
. OH
-
N
CH
3
CH
3
CH
3
CH
3
.. OH
-
ammonuim
hydroxide
tetra methyl
ammonuim
hydroxide
tetra alkyl ammonuim
hydroxide
N
C H
2 5
C H
2 5
C H
2 5
C H
2 5
.OH
tetra ethyl ammonuim
hydroxide

6. Nomenclature
common system
Primary amines
CH NH
3 2 C H NH
2 5 2 (CH )CH NH
methyl
amine
ethyl
amine
Iso propyl amine
1
0 0
3 2 2
1
0
1
Secondary amines
C H
5
NH
CH
HC
3
3
HN
C H
2 5
C H
2 5
HN
C H
dimethyl
amine
diethyl
amine
Ethyl propyl
amine
2 2
2
2
3 7
0
0
0
3
NCH
3
CH
3
CH
N
C H
2 5
Tertiary amines
Trimethyl
amine
3
0
0
CH
CH
3
3
ethyldimethylamine
mixed 3

7. IUPAC system
Primary amines
CH NH
3 2 C H NH
2 5 2
3
3
CH
CH
HC
NH2
methamaine
ethanamine propane-2-amine
Secondary amines
NH
CH
HC
3
3
N-methyl metha
namine
CH NH CH CH
323
N-methylethanamine
3
NCH
3
CH
3
CH
N
C H
2 5
Tertiary amines
0
0
CH
CH
3
3
N,N-dimethylethanamine
N,N-dimethylmethanamine
H
C CH CH
HC
NH
323
2
Butan-2 amine

8. Structure of
amines
H H
H
N
O O
107
0
Ammonia
3HC CH3
C
H3
N
O O
108
0
Trimethylamine
Fig:pyramidal shape of dimethylamine & trimethylamine

9. 3HC C3H7
C2H5
N
O O
N
O O
H3C
C3H7C2H5
rapid inversion
Fig:Enantiomers of methyl ethyl n-propyl amine
(I)
(II)

10. Preparation of
amines
• Reduction of nitro compounds
• Reduction of nitriles
• Reduction of oximes
• Reduction of amides
• Reductive amination of aldehydes & ketones
• Reduction of acyl halide

11. Reduction Of Nitro
Compounds
C H NO
2 5 2
+ 6(H) Sn
HCl
C H NH
2 5 2
+ 2H O
2
CH CH NO
3 2 2
LiAlH4
CH CH NH
3 2 2
NO2
CH3
NH2
CH3
H2,NI
NHCOCH3
NO2
NHCOCH3
NH2
H Pt
2

12. Reduction of
oximes
CH CH NOH
3
+ 4(H) CH CH NH
3 2 2
LialH4
+ H O
2
+ 4(H) LialH4 H2N
PROPAN 2 AMINE
3HC
H3C
NOH
propan-2-one oxime
+ H O
2
R
R
O
+ NH OH
2 CR
R
NOH
+ H O
2

13. Reduction of
nitriles &
amides
3HCC N + H2
Ni (CH CH NH)
3
H2
Ni
CH3
H2
C NH2
acetonitrile ethanamine
CH CH C N
3 2
LiAlH4 CH CH CH NH
3 2 2 2
hydrogen cyanide n propylamine
N+-
C
methyl isocyanide
LiAlH4
H
N
dimethylamine
acetamide
3HC NH2
O
CH3
H2
C
NH2
+ H O
2
ethanamine
LIAlH4
Ether
CH3 C NHCH3
O LIAlH4
Ether
CH3
H2
C NH CH3
+ H O
2

14. Reaction of
alkyl halides
• Hofmann”s method
CH3 CH2 I + NH3
CH3CH2 NH2 + HI
C H
6 5
Cl + 2NH
3
C H
6 5
NH
2
+ NH4Cl
Cuprous salt
473K

15. Reductive amination of
aldehydes & ketones
R C
H
O + NH3
-H2O
(R C
H
NH) R C
H
H
NH2
H2
Ni
imine
schiff"s
bases
Primary aminealdehyde
R C O
R
+ NH3
(R C NH)
R1 H2
Ni
R C
R1
H
NH2
secondary
amine
CH (CH2)5CHO CH (CH2)5 CH NH
2 23 3
NH3
H2-Ni
Heptaldehyde n heptyl amine
O
methyl ethyl ketone
NH3
H2-Ni
NH2
2-amino butane

16. Reduction of acyl halides
R C
O
Cl + NaN3
R C
O
N3 + NaCl
R C
O
N3
Heat
-N2
R N C O + NaCl
H2O
RNH2
+ CO
2

17. From
Phthalimide
NH
O
O
NK
O
O
RX
-KX N
O
O
R
H+H2O
O
O
OH
OH
+ RNH
2
phthalic acid
potassium salt of
phthalimidephthalimide
KOH

18. LETS GO AHEAD & SEE AGAIN