Benzyl Chloride → Ethylamine
Reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([Cl:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([N:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:5]([NH2:6])[CH3:4].[I:1][C:2]1[CH:8]=[CH:7][CH:5]=[CH:4][C:3]=1[CH2:9][Cl:16]Participants
Procedure
In a like manner p-iodoaniline and benzyl chloride were reacted to yield N,N-dibenzyl-p-iodoaniline, Rf =0.71, ethylamine and o-iodo-benzyl chloride were reacted to yield N-ethyl-o-iodobenzylamine, Rf =0.55, propylamine and o-iodo-benzyl chloride were reacted to yield N-propyl-o-iodobenzylamine, Rf =0.67, p-iodo-aniline and phenethyl bromide were reacted to yield N-β-phenethyl-p-iodoaniline, Rf =0.73, β-phenethylamine and o-iodobenzyl bromide were reacted to yield N-β-phenethyl-o-iodobenzylamine, Rf =0.64, N-β-phenethyl-o-iodo-benzylamine and phenethyl bromide were reacted to yield N,N-di-β-phenethyl-o-iodobenzylamine, Rf =0.64, ethylamine and o-iodobenzyl chloride were reacted to yield N,N-di-o-iodobenzylethylamine, Rf =0.80, 2,5-dimethylpyrrolidine and o-iodobenzyl chloride were reacted to yield N-o-iodobenzyl-2,5-dimethylpyrrolidine, Rf =0.78, and N-isopropyl-β-phenethylamine and o-iodo-benzyl bromide were reacted to yield N-β-phenethyl-o-iodo-β-phenethylamine, Rf =0.66.
Sources & evidence
- ORD record
- ord-290e81f2f06a429881aabb4cc656280d
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04360511
Reaction notes
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