Methylamine → (3-Methoxy)-alpha-methyl-alpha-[(methylamino)methyl]benzene methanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH3:12])[CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:13][NH2:14]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:12])([CH2:11][NH:14][CH3:13])[OH:10])[CH:6]=[CH:7][CH:8]=1Participants
3
Procedure
2-(3-Methoxyphenyl)-2-methyloxiran (34.0 g) was stirred with aqueous methylamine (100 ml, 33%) and alcoholic methylamine (200 ml, 33%) overnight at ambient temperature. The mixture was evaporated to an oil under reduced pressure, dissolved in hydrochloric acid (2 M) and extracted with toluene. After basifying the aqueous acid with sodium hydroxide (5 M) the basic oil was extracted with toluene and dried (MgSO4). The solvent was removed under reduced pressure to leave the title compound as an oil (27.7 g). The hydrochloride was formed in isopropyl alcohol-ethereal hydrogen chloride, m.p. 155°-156° C. (Found: C, 57.55; H, 8.3; N, 5.8% C11H17NO2HCl requires C, 57.0; H, 7.8; N, 6.0%.