Methanol → HCID 57878620, compound

To 2,3-dichlorobenzaldehyde (2.58 g, 19.2 mmol) in THF (5 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (1M in THF, 23 mL). The ice-water bath was removed and the reaction mixture was stirred from 0° C. to room temperature for 2 h. The reaction mixture was then cooled back to 0° C. and benzylmagnesium chloride (1M in THF, 23 mL) was added. The reaction mixture was stirred from 0° C. to room temperature for 1 h then quenched with NH4Cl (Sat.), extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. HCl (1.25M in methanol) was added to the above residue until a pH of 2 to form the amine salt solution. Methanol was removed to give yellow solid. To the solid was added dichloromethane. The suspension was filtered and washed with dichloromethane to yield white solid as pure amine salt. The amine salt was converted to free amine by dissolving the white solid in methanol, basified with NaOH (1N) and extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated to produce 1-(3-chloro-2-methylphenyl)-2-phenylethanamine (3.26 g, 75%) as light yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.57-2.65 (m, 1H), 3.11-3.17 (m, 1H), 4.68-4.72 (m, 1H), 7.20-7.35 (m, 6H), 7.36-7.40 (m, 1H), 7.51-7.54 (m, 1H).

1. extractionextracted with ethyl acetate
2. washCombined ethyl acetate was washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated

ORD record

ord-cc37195eef4f4e119bba2d594aedcee7

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183414B2