Oxyphencyclimine

Oxyphencyclimine is a muscarinic receptor antagonist, given orally to treat peptic ulcer disease and gastrointestinal spasms. It has antispasmodic and antimotility properties.

Synthesis

The reaction of chloroacetonitrile (1) with methanol and hydrogen chloride leads to the corresponding iminoether (Pinner reaction). Condensation of 2 with 3-methylaminopropylamine gives (3) gives the corresponding tetrahydropyrimidine (4). Displacement of the halogen with the sodium salt 5 affords oxyphencyclimine (6).

Oxyphencyclimine synthesis.[1][2]

References

  1. ^ Faust JA, Mori A, Sahyun M (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society. 81 (9): 2214. doi:10.1021/ja01518a051.
  2. ^ GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned to Charles Pfizer & Co. Inc.