Imidazole → [2-(1H-imidazol-1-yl)ethyl]methylamine dihydrochloride

HRID 1517175Notes

Reaction equation

HRID 1517175 reaction equation
S([O-])(=O)(=O)C.[NH:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>>[CH3:7][NH:6][CH2:10][CH2:9][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 85257MethanesulfonateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 6483896[2-(1H-imidazol-1-yl)ethyl]methylamine dihydrochloride

Procedure

1-[2-(N-methylamino)ethyl]imidazole was synthesized from the mesylate of 2-(N-Boc-N-methylamono)ethanol, which was allowed to react with imidazole in the presence of LiHMDS. The starting material was prepared by selective protection of amino group with Boc-anhydride in the presence of Al2O3 according to the procedure described in literature (Yadar, V. K.; Ganesh Babu, K. J. Org. Chem. 2004, 69, 577-580).

Sources & evidence

ORD record
ord-e5e95ce26b1a4fb7bf649d57e3d2e216
Source dataset
uspto-grants-2012_07
Patent number
US08232268B2

Reaction notes

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