Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1993-12-13
1995-08-15
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564303, C07B 5700
Patent
active
054421179
ABSTRACT:
A process for obtaining a substantially pure enantiomer of an hydrocarbyl amine is described. The process utilizes first an enantiomerically enriched mixture the of hydrocarbyl amine obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with an inorganic acid producing a salt that has the following properties:
1) has at least one eutectic point;
2) a composition that is not at the eutectic point; and
3) a eutectic composition that is closer to the racemic
composition than is the eutectic composition of said
hydrocarbyl, or be a solid where the salt is a liquid. A substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and the hydrocarbyl amine enriched in the other enantiomer.
REFERENCES:
patent: 4831147 (1989-05-01), Russell
patent: 4865770 (1989-09-01), Piselli
patent: 4931587 (1990-06-01), Piselli
patent: 4973745 (1990-11-01), Blaschke et al.
Collet et al., Chem. Rev. 80(3), 215-230 (1980).
Jacques et al., Enantiomers, Racemates and Resolutions, Chapter 3, J. Wiley & Sons, New York, N.Y., (1981) 167-213.
Collet, A., "The Homochiral Versus Heterochiral Packing Dilemma", 91-110 in Problems and Wonders of Chiral Molecules, Simonyi, M. (Ed.), Akademiai Keado, Budapest (1990).
Manimaran Thanikavelu
Stahly G. Patrick
Albemarle Corporation
O'Sullivan Peter
Pippenger Philip M.
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