Oxyphencyclimine

Oxyphencyclimine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A03AA01 (WHO) ;
Identifiers
	IUPAC name (1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate;
CAS Number	125-53-1 ;
PubChem CID	4642;
IUPHAR/BPS	7256;
ChemSpider	4481 ;
UNII	4V44H1O8XI;
KEGG	D08325 ;
ChEMBL	ChEMBL1200891 ;
CompTox Dashboard (EPA)	DTXSID4023410 ;
ECHA InfoCard	100.004.313
Chemical and physical data
Formula	C20H28N2O3
Molar mass	344.455 g·mol−1
	InChI InChI=1S/C20H28N2O3/c1-22-14-8-13-21-18(22)15-25-19(23)20(24,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2,4-5,9-10,17,24H,3,6-8,11-15H2,1H3 ; Key:DUDKAZCAISNGQN-UHFFFAOYSA-N ;
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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

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).

References

↑ Faust JA, Mori A, Sahyun M (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society. 81 (9): 2214–2219. doi:10.1021/ja01518a051.
↑ GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned to Charles Pfizer & Co. Inc.

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[1] Faust JA, Mori A, Sahyun M (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society. 81 (9): 2214–2219. doi:10.1021/ja01518a051.

[2] GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned to Charles Pfizer & Co. Inc.

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Synthesis

References