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PHMD102-Amines_150142.pptx

Amines are organic compounds derived from ammonia where one or more hydrogen atoms are replaced by alkyl or aryl groups. They are classified as primary, secondary, tertiary, or quaternary depending on the number of alkyl/aryl substitutions. Amines can be synthesized through reactions of alkyl halides with ammonia, reduction of alcohols or nitriles with ammonia, or reduction of nitroalkanes or amides. Their properties depend on structure, with lower alkyl amines being gases or liquids and higher ones solids. Amines react with acids, acid chlorides, and nitrous acid. They have many pharmaceutical uses as analgesics, anesthetics, and in creating amino acids.

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AMINES
Introduction And classification ■ Amines are derivatives of ammonia in which one or more hydrogens are replaced with alkyl or aryl groups. ■ Alkyl-substituted (alkylamines) or aryl- substituted (arylamines) ■ Classified: – 1° (RNH2) Primary amine – 2° (R2NH) Secondary amine – 3° (R3N) Tertiary amine – 4° (𝑹𝟒N) Quaternary amine They are actually quaternary ammonium salts N H H R N R H R N R R R Primary Secondary Tertiary N R R R R X Quaternar y
nomenclature ■ For simple amines, the suffix -amine is added to the name of the alkyl substituent NH2 tert-butylamine H2N cyclohexanamine H2N NH2 1,4-butandiamine N H3C N-Methyl-Cyclohexanamine H N N N,N-Dimethyl-4-aminopyridine IUPAC Names – Simple Amines
IUPAC Names – Amines With More Than One Functional Group nomenclature ■ Consider the NH2 as an amino substituent on the parent molecule
synthesis 1) Reaction of alkyl halide with ammonia ■ CH3I + H-NH2 → CH3NH2 + HI 2) Reduction of alcohol with ammonia (In presence of Al2O3 and 400C) CH3OH + H-NH2 → CH3NH2 + H2O
synthesis 3) REDUCTION OF NITROALKANE: (in presence of pt/Ni/ LiAl H4) CH3NO2 + 3H2 → CH3NH2 + 2H2O 4) REDUCTION OF NITRILES: (in presence of LiAl H4 and ether) CH3C≡N + 4 [H] → CH3CH2NH2 5) REDUCTION OF AMIDES: (in presence of LiAl H4 and ether) CH3CONH2 + 4 [H] → CH3CH2NH2 + H2O
Physical properties  The lower aliphatic amines are gaseous in nature and they have fishy smell  Primary amines with three or four carbons are liquid in nature whereas higher ones are solids  They get color due to oxidation in open environment  Lower aliphatic amines can form hydrogen bonds with water thus they are water soluble  Soluble in benzene, ether etc  Increase in size of hydrophobic alkyl part increases in molar mass and ultimately boiling point increases  In tertiary amines there is no inter-molecular association due to absence of hydrogen atom for H-bonding so no solubility in water is there.
Chemical properties 1) Salt Formation 2) Reaction with acid chloride CH3 − NH2 + CH3-CO-Cl → CH3 − CO − NH − CH3 + HCl N-methyl acetamide CH3CH2NH2 + HCl → CH3CH2-NH3+ Cl-
Chemical properties 3) Reaction with Nitrous Acid  Primary amines react with nitrous acid to form alcohols and nitrogen gas. 𝑅 − 𝑁𝐻2 + 𝐻𝑂𝑁𝑂 → 𝑅𝑂𝐻 + 𝑁2 ↑ + 𝐻2𝑂 𝐶2𝐻5 −𝑁𝐻2 + 𝐻𝑂𝑁𝑂 → 𝐶2𝐻5𝑂𝐻 + 𝑁2 ↑ + 𝐻2𝑂 ethylamine Ethyl alcohol
Pharmaceutical uses  Amines are largely used in pharmaceutical industry  Morphine and Demerol are used as analgesics that are pain killers  Novocaine is used as anesthetic.  Tetramethyl ammonium iodide for disinfecting drinking water  These are involved in the creation of amino acids which are the building blocks of proteins.  Many amines are used in industry for pest control and tanning of leather.  Many vitamins are also built from amino acids.