Exercício de Química Sintética e Organica Mista (631)

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(d) Acetyl chloride reacts with benzylamine to form an amide.
(e) Acetic anhydride also gives an amide with benzylamine.
( f ) Primary amines react with ketones to give imines.
(g) These reaction conditions lead to reduction of the imine formed in part ( f ). The overall reac-
tion is reductive amination.
(h) Amines are nucleophilic and bring about the opening of epoxide rings.
(i) In these nucleophilic ring-opening reactions the amine attacks the less sterically hindered car-
bon of the ring.
( j) With excess methyl iodide, amines are converted to quaternary ammonium iodides.
C6H5CH2NH2 �
Benzylamine
C6H5CH2N(CH3)3 I
�
Benzyltrimethylammonium
iodide
Methyl
iodide
3CH3I
�
C6H5CH2NH2 C6H5CH2NHCH2CHCH3�
Benzylamine 1-(N-Benzylamino)-2-propanol1,2-Epoxypropane
H2C CHCH3
O OH
C6H5CH2NH2 C6H5CH2NHCH2CH2OH�
Benzylamine 2-(N-Benzylamino)ethanolEthylene oxide
H2C CH2
O
C6H5CH2NH2 (CH3)2CHNHCH2C6H5CH3CCH3
O
�
Benzylamine Acetone N-Isopropylbenzylamine
H2, Ni
C6H5CH2NH2 (CH3)2CCH3CCH3
O
�
Benzylamine Acetone N-Isopropylidenebenzylamine
NCH2C6H5
2C6H5CH2NH2 CH3CNHCH2C6H5CH3COCCH3
O O O
� �
Benzylamine Acetic anhydride N-Benzylacetamide
O
C6H5CH2NH3 
�OCCH3
Benzylammonium acetate
�
2C6H5CH2NH2 CH3CNHCH2C6H5CH3CCl
O O
� �
Benzylamine Acetyl
chloride
N-Benzylacetamide
C6H5CH2NH3 Cl
�
�
Benzylammonium
chloride
626 AMINES