Bis(trifluoroacetoxy)iodobenzene → 4-[[(2,2-Dimethyl-1-oxopropyl)amino]methyl]benzeneethanamine
Reaction equation
[NH2:1]CC1C=CC(CCC(O)=O)=CC=1.[CH3:14][C:15]([CH3:32])([CH3:31])[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27]C(N)=O)=[CH:22][CH:21]=1)=[O:17].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>>[CH3:14][C:15]([CH3:32])([CH3:31])[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH2:1])=[CH:22][CH:21]=1)=[O:17]Participants
Procedure
4-Cyanocinnamic is catalytically hydrogenated to form 4-(aminomethyl)-benzenepropanoic acid, the amino function is then protected by a tert.butoxycarbonyl group and the carboxylic acid function is converted into the primary carboxamide; the resulting 4-[[(2,2-dimethyl-1-oxopropyl)amino]methyl]benzenepropanamide when reacted with I,I-bis-(trifluoroacetoxy)iodobenzene, yields 4-[[(2,2-dimethyl-1-oxopropyl)amino]methyl]benzeneethanamine (see also: A. S. Radhakrishna, M. E. Parham, R. M. Riggs and G. M. Loudon, J. Org. Chem. 44: 1746-1747 (1979) and K. Seraminathan and N. Venkatasubramanian, J. Chem. Soc. Perkim Trans. II 1975, 1161), which may be converted into the corresponding urea in the usual way, e.g. by treating the hydrochloride with sodium cyanate; cleaving the tert.butoxycarbonyl group with suitable acids, e.g. trifluoroacetic acid, finally yields the desired 4-[2-(aminocarbonylamino)ethyl]phenylmethanamine.
Sources & evidence
- ORD record
- ord-823075ccabc74d73bc388fc770a2be69
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114390
Reaction notes
Loading…