Hoch-Campbell ethylenimine synthesis

In organic chemistry the Hoch-Campbell ethylenimine synthesis is a method for constructing ethyleneimines from oximes. The oxime is treated with Grignard reagents: ^{[1] [2] [3] [4]}

Hoch-Campbell Ethylenimine Synthesis

The above product is called 3-methyl-2,2-diphenylaziridine [7764-13-8]. A compound that is described is called 2-amino-1,1-diphenylpropan-1-ol [57728-35-5]. This is an open-chain analog of pipradrol. 99% of the theoretical yield can be achieved by Grignard addition of two equivalents of phenylmagnesium bromide to alanine ethyl ester. This compound has remarkable similarity to Diphepanol, which is based on a piperidine and not a primary amine.

N.B. Joseph Hoch was the first chemist to invent diphenylacetonitrile.

References

1. (a), Hoch, Compt. rend., 196, 1865 (1934); (b), ibid., 203, 799 (1936); (c), ibid., 204, 358 (1937).
2. Kenneth N. Campbell; James F. Mckenna (1939). "The action of Grignard reagents on oximes. i. The action of phenylmagnesium bromide on mixed ketoximes". Journal of Organic Chemistry . 4 (2): 198–205. doi:10.1021/jo01214a012.
3. Kenneth N. Campbell; Barbara Knapp Campbell; Elmer Paul Chaput (1943). "The reaction of Grignard reagents with oximes. ii. The action of aryl grignard reagents with mixed ketoximes". Journal of Organic Chemistry . 8 (1): 99–102. doi:10.1021/jo01189a015.
4. Kenneth N. Campbell; Barbara K. Campbell; James F. Mckenna; Elmer Paul Chaput (1943). "The action of Grignard reagents on oximes. iii. The mechanism of the action of arylmagnesium halides on mixed ketoximes. A new synthesis of ethyleneimines". Journal of Organic Chemistry . 8: 103–9. doi:10.1021/jo01189a016.