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ECHA InfoCard | 100.004.313 |
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Formula | C20H28N2O3 |
Molar mass | 344.455 g·mol−1 |
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Oxyphencyclimine is a muscarinic receptor antagonist, given orally to treat peptic ulcer disease and gastrointestinal spasms. It has antispasmodic and antimotility properties.
Synthesis[edit]
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).
![](https://upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Oxyphencyclimine_synthesis.svg/500px-Oxyphencyclimine_synthesis.svg.png)
References[edit]
- ^ 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.
- ^ GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned to Charles Pfizer & Co. Inc.