Synthesis of diacetonamine (diacetonamine hydrogenoxalate)

Preparation of diacetonamine

Preparation of diacetonamine (diacetonamine hydrogenoxalate)

Preparation of diacetonamine (diacetonamine hydrogenoxalate)

50 ml of mesityl oxide are dissolved in 100 ml of alcohol, cooled in a freezing mixture to -10° C, and dry ammonia is passed into the solution until saturated. The solution is allowed to stand for 48 hours. The diacetonamine base is separated as the acid oxalate. 30 g of powdered oxalic acid are mixed with 120 ml of alcohol in a beaker placed in ice. The ammoniacal solution is gradually added with vigorous stirring so that the temperature does not rise above 20° C until the pasty mass is neutral. To the resulting mixture, which is nearly solid, further 30 g of powdered oxalic acid are added and stirred. The reaction mixture is poured in a round bottom flask fitted with reflux condenser and boil for 15 minutes to complete the reaction. The diacetonamine hydrogenoxalate is filtered hot and the solution cooled slowly to 0° C. The diacetonamine hydrogenoxalate separates in crusts, which are filtered. The yield from 50 ml of mesityl oxide is about 50 g of diacetonamine hydrogenoxalate. Diacetonamine can also be prepared directly by the action of ammonia on acetone.

A Class-Book of Organic Chemistry, by J. B. Cohen, 12, 1919

IUPAC Name

4-amino-4-methylpentan-2-one

InChI

InChI=1S/C6H13NO/c1-5(8)4-6(2,3)7/h4,7H2,1-3H3

InChI Key

CQTRUFMMCCOKTA-UHFFFAOYSA-N

Canonical SMILES

CC(=O)CC(C)(C)N

MeSH Synonyms

diacetonamine

Depositor-Supplied Synonyms

Diacetonamine, 2-Pentanone, 4-amino-4-methyl-, 4-Amino-4-methylpentan-2-one, 4-Amino-4-methyl-2-pentanone, UNII-WI13YZU3HT, WI13YZU3HT, AC1L2BP2, AC1Q5CG5, SCHEMBL690783, AC1Q1K45, CQTRUFMMCCOKTA-UHFFFAOYSA-N, MolPort-001-779-724, EINECS 210-876-8, AR-1I3735, AKOS006220717, 4CN-0963, 4-Amino-4-Methyl-2-Pentanone Hydrogen Oxalate, L-1557, 4-AMINO-4-METHYL-2-PENTANONEHYDROGENOXALATE, S14-1063, 3B3-049810

Removed Synonyms

CID69361, 625-04-7, 6342-21-8

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