Norephedrine 2 -Amino-1-phenyl-1-propanol

SYNS a-(l-AMINOETHYL)BENZENEMETHANOL HYDROCHLORIDE a-(l-AMINOETHYL)BENZYL ALCOHOL HYDROCHLORIDE ( )-2-AMINO-l-PHENYL-l-PROPANOL HYDROCHLORIDE O-HYDROXY-P-AMINOPROPYLBENZENE HYDROCHLORIDE MONHYDRIN MUCORAMA MYDRIATINE dl-NOREPHEDRINE HYDROCHLORIDE dl-l-PHENYL-2-AMINO-l-PROPANOL MONOHYDROCHLORIDE PHENYLPROPANOLAMINE HYDROCHLORIDE... 

Common Name dl-norephedrine hydrochloride 2-amino-1-phenyl-1-propanol hydrochloride... 

Common Name dl-Norephedrine hydrochloride 2-Amino-l-phenyl-l-propanol hydrochloride... 

Hoover and Hass hydrogenated 2-nitro-l-phenyl-l-propanol over Raney Ni in ethanol in the presence of sufficient carbon dioxide to produce a pressure of 2.1 MPa and obtained the corresponding amino alcohol (a mixture of /-norephedrine and dl-norisoephedrine) in 87% yield.18 The formation of /V-ethylbenzylamine, a byproduct, was depressed to 5% under these conditions (eq. 9.6). Without carbon dioxide the yield of /V-clhylbcnzylaminc was approximately 45%. 

Ephedrine anhyd. (-)-Pseudoephedrine (-)-Norephedrine (+)-2-Amino-3-methoxy-1 -phenyl -1 -propanol... 

DL-( )-Norephedrine hydrochloride [Propadrin, ( )- ijtAro-lJ. , 2 / -2-amino-l-phenyl-l-propanol hydrochloride] [154-41-6] m 194-196° (also 194° was reported), pK 8.20. It crystallises in plates from absolute EtOH or isoPrOH, and the )-oxalate has m 245°(dec) (plates from H2O). The 2,4-dinitrobenzoate has m 86-88° (from EtOH) and the 3,5-dinitrobenzoate has m 78-79° (from EtOH). It is a mixed anti-sympathomimetic and used as a nasal anticongestant. [cf Atkins Cramer J Am Chem Soc 52 4349 1930, Krantz Hartimg JA/w Pharm Assoc 19 461 1930, Fischer Plein JA/w Pharm Assoc 44 313 1955, Beilstein 13 I 252,13II371,13 III 1717,13 IV 1875.]... 

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