99558-03-9

Upstream product

• 59473-45-9 2-(chloromethyl)iodobenzene 
• 109-89-7 diethylamine 
• 76041-87-7 N,N-diethyl-2-iodobenzamide 
• 40400-13-3 2-Iodobenzyl bromide 
• 64-17-5 ethanol 
• 615-37-2 ortho-methylphenyl iodide 

Downstream Products

• 138154-64-0 2-(Benzyl-ethyl-amino)-3-ethyl-pentan-3-ol 
• 382153-28-8 (ortho-C₆H₄CH₂N(C₂H₅)2)PdI(bis(diphenylphosphino)propane) 
• 382153-18-6 PdI(ortho-C₆H₄(CH₂N(C₂H₅)2))(P(C₆H₅)3) 
• 382153-16-4 trans-PdI(ortho-C₆H₄(CH₂N(C₂H₅)2))(P(C₆H₅)3)2 
• 1224733-34-9 N-benzyl-N-ethyl-1-(pyridin-3-yl)ethanamine 
• 1224733-32-7 N-benzyl-N-ethyl-1-(2-methylphenyl)ethanamine 
• 1224733-27-0 N-benzyl-N-ethyl-1-(4-fluorophenyl)ethanamine 
• 1224733-38-3 1,1-dideuterio-N-(1-deuterio-1-(4-fluorophenyl)ethyl)-N-(2-deuteriobenzyl)ethanamine 
• 112-40-3 dodecane 
• 1224733-37-2 N-benzyl-N-ethylheptan-2-amine 
• 1224733-42-9 N₂,N₃-dibenzyl-N₂,N₃-diethylbutane-2,3-diamine 
• 1224733-36-1 N-benzyl-N-ethyl-4-methylpent-3-en-2-amine 
• 1224733-35-0 N-benzyl-N-ethyl-3-methylbut-3-en-2-amine 
• 1224733-29-2 N-benzyl-N-ethyl-1-(4-chlorophenyl)ethanamine 

Relevant academic research and scientific papers

α-Alkylation of Amines via a 1,5-Hydrogen Shift

Radicals derived from N-(2-iodobenzyl) 'protected' amines undergo a 1,5-hydrogen shift to give more stable α-amino radicals, which can be subsequently trapped by electron deficient alkenes.

Radioiodinated analogs of xylamine: N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine and N,N-diethyl-2-[125I)iodo benzylamine as potential tools for monoamine uptake exploration by SPECT

In order to improve the scintigraphy and radiotherapy of neuroendocrine tumors we synthesized two radioiodinated benzylamines [N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine and N,N-diethyl-2-[125I]iodobenzylamine], analogs of xylamine [N-(2-chloroethyl)-N-ethyl-2-methylbenzylamine]. Xylamine is an irreversible inhibitor of uptake and accumulation of noradrenaline. The two unlabelled iodinated derivatives [N-(2-chloroethyl)-N-ethyl-2-iodobenzylamine and N,N-diethyl-2-iodobenzylamine] were synthesized, purified and checked by HPLC, NMR and mass spectrography. Their affinity for the noradrenaline transporter was determined in vitro on rat brain membrane homogenates with [3H]nisoxetine. Radioiodination was performed by iodide for bromide nucleophilic exchange from brominated precursors. The N,N-diethyl-2-[125I]iodobenzylamine was obtained directly from N,N-diethyl-2-bromobenzylamine. Radiosynthesis of N-(2-chloroethyl)-Nethyl-2-[125I]iodobenzylamine required three steps. A new brominated precursor [N-ethyl-N-(2-bromobenzyl)glycine ethyl ester] which was stable for radiolabelling and suitable for reduction to N-(2-hydroxyethyl)-N-ethyl-2-[125I]iodobenzylamine was synthesized. N-(2-Hydroxyethyl)-N-ethyl-2-[125I]iodobenzylamine was converted to N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine in the presence of an excess of thionyl chloride. Radioiodinated derivatives were purified and checked by HPLC.

An approach to α-substituted amines

A number of amines have been alkylated at the position alpha to nitrogen via free radical methodology. N-(2-iodobenzyl) and N-(2-iodobenzoyl) 'protected' amines have been used to generate radicals which rapidly undergo a 1,5-hydrogen shift to give more st

Generation and Alkylation of Carbanions α to the Nitrogen of Amines by a New Metalation Procedure

Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates α-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bond formation products in good yield.

11H-Isoindoloindol-11-ones: Novel Rearrangement Products from the Attempted Preparation of 2-(2-Diethylaminomethylphenyl)isatogens

The attempted synthesis of 2-(2-diethylaminomethylphenyl)isatogens, from appropriately substituted phenylacetylenes and aromatic iodo compounds by two different routes gave novel substituted 11H-isoindoloindol-11-ones (6a-d) as the only identifiabl