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 ;
ECHA InfoCard	100.004.313
Chemical and physical data
Formula	C20H28N2O3
Molar mass	344.45 g/mol
	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 an antimuscarinic.

Synthesis

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] GB 795758 (1958 to Pfizer).

References

↑ Faust, J. A.; Mori, A.; Sahyun, M. (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society. 81 (9): 2214. doi:10.1021/ja01518a051.

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