Oxyphencyclimine

Oxyphencyclimine

Systematic (IUPAC) name
(1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	125-53-1 Y
ATC code	A03AA01 (WHO)
PubChem	CID: 4642
IUPHAR/BPS	7256
ChemSpider	4481 N
UNII	4V44H1O8XI N
KEGG	D08325 Y
ChEMBL	CHEMBL1200891 N
Chemical data
Formula	C20H28N2O3
Molecular 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 N Key:DUDKAZCAISNGQN-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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: GB 795758  (1958 to Pfizer).