1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. This primary amine is a colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.

Preparation and optical resolution

1-Phenylethylamine may be prepared by the reductive amination of acetophenone:[1]

C6H5C(O)CH3 + NH3 + H2 → C6H5CH(NH2)CH3 + H2O

The Leuckart reaction, using ammonium formate, is another method for this transformation.[2]

L-malic acid is used to resolve 1-Phenylethylamine, a versatile resolving agent in its own right. The dextrorotatory enantiomer crystallizes with the malate, leaving the levorotatory form in solution.[3]

See also

References

  1. ^ John C. Robinson, Jr. and H. R. Snyder (1943). "α-Phenylethylamine". Organic Syntheses. 23: 68. doi:10.15227/orgsyn.023.0068.
  2. ^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN 9780582444072.
  3. ^ A. W. Ingersoll (1937). "d- and l-α-Phenylethylamine". Organic Syntheses. 17: 80. doi:10.15227/orgsyn.017.0080.