7308. Phenylpropylmethylamine

Nomenclature

CAS number: 93-88-9
N,β-Dimethylbenzeneethanamine; dl-N,β-dimethylphenethylamine; dl-N-methyl-2-phenylpropylamine; 1-methylamino-2-phenylpropane; phenpromethamine; 1-methylamino-2-methyl-2-phenylethane; Vonedrine.
C10H15N; mol wt 149.23.
C 80.48%, H 10.13%, N 9.39%.

Description and references

Synthesis starting with the condensation of chlorobenzene with allyl chloride, followed by ammonolysis: Patrick et al., J. Am. Chem. Soc. 68, 1009 (1946).

Chemical structure

Properties

Volatile liquid. d425 0.915-0.925; bp760 205-210°; bp15 95-96°; nD20 1.5102. Slightly sol in water (1.2 g/100 ml). Freely sol in alcohol, ether, benzene. Aq solns are strongly alkaline; pH of a soln of 2 drops (≈0.1 ml) dil with 10 ml H2O is ≈10.5.

Derivative

Hydrochloride.
C10H15N.HCl; mol wt 185.69.
C 64.68%, H 8.68%, N 7.54%, Cl 19.09%.

Properties

mp 144-148°.

Therapeutic Category

Adrenergic.

Keywords

α-Adrenergic Agonist; Decongestant