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Aliphatic amines part i
- 1. ALIPAHTIC AMINES • Unit-VI&POC I • II SEM B.PHARM • Aliphatic amines part I • 06.07.2020
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- 3. Definition • Amines arederivatives Of ammonia in which one or more hydrogen atoms have been replaced by alkyl or aryl groups N H H H Ammonia N H H CH 3 N CH H CH 3 3 N CH CH CH 3 3 3 Methyl amine dimethyl amine trimethyl amine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 • Primaryamine: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 CHNH 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 CHNH 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 OO 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 OO H3C C3H7C2H5 rapid inversion Fig:Enantiomers of methyl ethyl n-propyl amine (I) (II)
- 10. Preparation of amines • Reductionof 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 CH 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 CHNOH 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 3HCCN + 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 acylhalides 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 phthalicacid potassium salt of phthalimidephthalimide KOH
- 18. LETS GO AHEAD& SEE AGAIN