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Merck
CN

A facile one-pot process for the formation of hindered tertiary amines.

Molecules (Basel, Switzerland) (2012-05-05)
Zhouyu Wang, Dong Pei, Yu Zhang, Chao Wang, Jian Sun
ABSTRACT

A simple and convenient method was developed for the preparation of hindered tertiary amines via direct reductive amination of ketones with secondary aryl amines, using trichlorosilane as reducing agent and tetramethylethylenediamine (TMEDA) as organic Lewis base activator. A broad range of ketones were reacted with N-methylaniline to afford the corresponding tertiary amine products in high yield. An open transition model was proposed for the reductive step.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N-Methylaniline, 98%
Sigma-Aldrich
N-Methylaniline, ≥99%
Sigma-Aldrich
N-Methylaniline, purum, ≥98.0% (GC)
Supelco
N-Methylaniline, analytical standard
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, ≥99.5%, purified by redistillation
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, ReagentPlus®, 99%
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, BioReagent, Molecular Biology, ≥99% (GC)
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, BioReagent, suitable for electrophoresis, ≥99.0%