Methanol → 1-(3-Methoxyphenyl)propan-1-amine

A flame-dried 250 mL R.B. flask equipped with a reflux condenser was charged, under argon, with 3-methoxybenzonitrile (2 g, 15 mmol) and dry THF (33.5 mL). Ethylmagnesium bromide (1 M) in THF (16.5 mL, 16.5 mmol) was then added followed by copper (I) bromide (43 mg, 0.3 mmol). The reaction mixture was refluxed for 30 min and then cool down to 0° C. before MeOH (0.61 mL, 15 mmol) was added. The reaction mixture was stirred for 10 min before LAH (1M) in THF (30 mL, 30 mmol) was added and stirred for 60 min at room temp. The reaction was quenched with an aqueous 2M solution of Rochelles' salts (200 mL), stirred for 60 min at room temperature, extracted with diethyl ether (4×30 mL), the organic extracts dried, filtered and concentrated to give the product (2.37 g, 96%) which was sufficiently pure for the next step. 1H NMR (400 MHz, methanol-d4) δ: 0.85 (t, 3H, J=7.4 Hz), 1.68-1.77 (m, 2H), 3.70 (dd, 1H, J=6.6 Hz), 3.81 (s, 3H), 6.81 (d, 1H, J=8.2 Hz), 6.90 (d, 1H, J=8.0 Hz), 6.91 (s, 1H), 7.24 (t, 1H, J=7.8 Hz).

1. customflask equipped with a reflux condenser
2. temperatureThe reaction mixture was refluxed for 30 min
3. additionwas added
4. additionwas added
5. customThe reaction was quenched with an aqueous 2M solution of Rochelles' salts (200 mL)
6. stirringstirred for 60 min at room temperature
7. extractionextracted with diethyl ether (4×30 mL)
8. customthe organic extracts dried
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-f1ac433d68154b28b96cbd673de90969

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090651B2