Methylamine → 1-(3-Methoxyphenyl)-N-methylethanamine

Titanium(IV) isopropoxide (130 ml) was added to a methanolic methylamine solution (125 ml, 8M) followed by the addition of 3-methoxybenzophenone (50 g). The reaction mixture was stirred at room temperature for 5 hours, after which sodium borohydride (12 g) was carefully added at 0-5° C. The mixture was stirred at room temperature for 2 hours, after which water (60 ml) was added. The inorganic precipitate was filtered off and the filtrate concentrated to dryness. The residue was partitioned between ethyl acetate (400 ml) and aqueous hydrochloric acid (2M, 400 ml). The aqueous phase was made alkaline (pH 11-12) and extracted with dichloromethane (2×300 ml). The organic phase was dried and concentrated to dryness, leaving 1-(3-methoxyphenyl)-N-methylethylamine (43.4 g) as a viscous oil.

1. stirringThe mixture was stirred at room temperature for 2 hours
2. filtrationThe inorganic precipitate was filtered off
3. concentrationthe filtrate concentrated to dryness
4. customThe residue was partitioned between ethyl acetate (400 ml) and aqueous hydrochloric acid (2M, 400 ml)
5. extractionextracted with dichloromethane (2×300 ml)
6. customThe organic phase was dried
7. concentrationconcentrated to dryness

ORD record

ord-d91dfa7fb3724a34919901491a62c8b0

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044067B2