Reaction Steps
Similar reaction of 4-[4-(N,N-bis(2-chloroethyl)-amino]phenyl)butanoic acid (VIII, n=3) [Everett, J. L., Roberts, J. J., Ross W. C. J., "Aryl-2-halogenoalkylamines. Part XII. Some carboxylic acid derivatives of N,N-di-2-chloroethylaniline", J. Chem. Soc., 1953 2386-2392] (4.75 g, 15.6 mmol) according to the above protocol gave 4[4-(N,N-bis(2-chloroethyl)amino)phenyl]butanal (IX, n=3) as a pale yellow oil (3.3 g, 73% overall yield). 1H NMR (CDCl3) δ 9.75 (t, J1,2 =1.6 Hz, 1 H, CHO), 7.06 (d, J2',3' =8.6 H z, 2 H, H-2',H-6'), 6.63 (d, J2',3' =8.6 Hz, 2 H, H-3', H-5=), 3.71 (t, J=7.4 Hz, 4 H, NCH2CH2Cl), 3.63 (t, J=7.4 Hz, 4 H, NCH2CH2Cl), 2.56 (t, J3,4 =7.4 Hz, 2 H, H-4), 2.45 (dt, J2,3 =7.3 Hz, and J1,2 =1.6 Hz, 2 H, H-2), 1.90 (quintet, J=7.4 Hz, 2 H, H-3). 13C NMR δ 202.52, 144.41, 130.28, 129.62, 112.21, 53.51, 43.10, 40.59, 33.82, 23.85. HRMS (EI, 70 eV) calcd for C14H19NO35Cl2 : 287.08437. Found: 287.08427.
