15597.eh21.373-38811/7/0514:47Page394 ⊕一 EQA 384.chapter 21 AMINES AND THEIR DERIVATIVES:FUNCTIONAL GROUPS CONTAINING NITROGEN First is (reversible)imine formation: CH=O+HNR→CH=NR+HO Then reduction gives the secondary amine: NaBHaCN CH2-NR-CHa-NHR Another CH2=O reacts,forming an iminium ion: CH2=0+HN(CH3)R-CH2=N(CH3)R +HO Reduction of this then gives the final product.a dimethylated amine: NaBH;CN+CH2-N(CH3)R-(CHa)2NR OH 子CH2一NH cn. -CH +CH2-N2H O. CO.H HFirst is (reversible) imine formation: CH2PO
H2NR 88n CH2PNR
H2O Then reduction gives the secondary amine: NaBH3CN
CH2PNR 88n CH3ONHR Another CH2PO reacts, forming an iminium ion: CH2PO
HN(CH3)R 88n CH2PN
(CH3)R
HO Reduction of this then gives the final product, a dimethylated amine: NaBH3CN
CH2PN
(CH3)R 88n (CH3)2NR 51. CH2 CH CO2H O CH products H
H
HN H CH2 C H
, H2O H
H
CO2H N CH H HOCH2 OH N CH3 CH2 C CO2H N H CH HOCH2 OH N CH3 Isomeric imine CH2 CH2 CO2H N C CH2 C
H
, H2O H
H
OH2 H CO2H N CH H HOCH2 OH N CH3 Imine CH2 CH2 CO2H NH2 C O
Proton transfers HOCH2 CH2NH2 OH N CH3
CH2 C CO2H O 384 • Chapter 21 AMINES AND THEIR DERIVATIVES: FUNCTIONAL GROUPS CONTAINING NITROGEN 1559T_ch21_373-388 11/7/05 14:47 Page 384