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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 16
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Original Articles

Safe and Efficient Reductive Methylation of Primary and Secondary Amines Using N-Methylpyrrolidine Zinc Borohydride

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Pages 2415-2420 | Received 03 Aug 2009, Published online: 26 Jul 2010
 

Abstract

An efficient, general procedure for reductive methylation of primary and secondary amines with 37% formaldehyde using N-methylpyrrolidine zinc borohydride (ZBHNMP) as a reducing agent gave the corresponding tertiary amines in excellent yields. The reaction was carried out in tetrahydrofuran under neutral conditions at 0–10 °C.

ACKNOWLEDGMENT

Financial support of this work from the Research Council of Mazandaran University is gratefully acknowledged.

Notes

a All reactions were carried out in THF at 0–10 °C, and the molar ratio of amine/formaldehyde/reductant was 2:1:4.

b All products were characterized spectroscopically (1H NMR, IR) and showed physical and spectral data in accordance with their expected structure by comparison with authentic samples.

c Yields refer to pure isolated products.

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