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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1070515Generated: October 30, 2026

Methyl iodide → N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

https://huagongshe.com/reaction/1070515

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantTriethylamineHCID 8471—
ReactantN-BOC-ethylenediamineHCID 187201—
SolventTetrahydrofuranHCID 8028—
ProductN-(tert-Butoxycarbonyl)-N'-methylethylenediamineHCID 3435744—

Reaction Steps

To a solution of (2-amino-ethyl)-carbamic acid-tert-butyl ester (5 g) and triethylamine (6.5 ml) in tetrahydrofuran (1000 ml) at 0° C. was added methyliodide (1.94 ml) dropwise over a period of 1 hour. The mixture was allowed to warm to ambient temperature and stirred for 72 hours before removal of solvents by evaporation. The residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and solvent removed by evaporation to give the title compound (3.7 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06903085B1
Source datasetuspto-grants-2005_06
ORD IDord-499fb470ffe7411c96892cf2a8e76613
Source noteuspto-grants-2005_06