Organic Reactions Volume 4 - Sciencemadness Dot Org

CHAPTER 3
THE PREPARATION OF AMINES BY REDUCTIVE
ALKYLATION
WILLIAM S. EMERSON
Monsanto Chemical Company
Dayton, Ohio
CONTENTS
PAGE
INTRODUCTION 175
SCOPE AND UTILITY OP THE REACTIONS 178
Preparation of Primary Amines 178
From Aliphatic Aldehydes 178
From Aromatic Aldehydes 179
From Ketones 180
Preparation of Secondary Amines 180
From Ammonia and Aliphatic Aldehydes and Ketones 180
From Ammonia and Aromatic Aldehydes 181
From Primary Amines and Carbonyl Compounds 181
Aliphatic Amines and Aldehydes 182
Aliphatic Amines or Nitro Compounds and Ketones 183
Aromatic Amines and Aldehydes; Aromatic Nitro Compounds, Azo
Compounds, etc., and Aldehydes 185
Aromatic Amines, Aromatic Nitro, Nitroso, or Azo Compounds and
Ketones 188
Preparation of Secondary Amines by Reduction of SchifPs Bases 189
From SchifT's Bases Derived from Aliphatic Amines 190
From SchifTs Bases Derived from Aromatic Amines 191
Preparation of Tertiary Amines 192
From Ammonia and Aldehydes and Ketones 192
From Primary Aliphatic Amines or Primary Aliphatic Nitro Compounds
and Aldehydes and Ketones 192
From Primary Aromatic Amines, Nitro Compounds, or Azo Compounds
and Aldehydes and Ketones 193
From Secondary Aliphatic Amines and Aldehydes and Ketones . . . . 194
From Secondary Aromatic Amines and Aldehydes and Ketones . . . . 195
SELECTION OF EXPEKIMENTAL CONDITIONS 196
Primary Amines 196
Secondary Amines 196
Tertiary Amines , . . . . 198
174