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TCI Practical Example: Reductive Amination Reaction Using Sodium Triacetoxyborohydride

We are proud to present reductive amination reaction of m-anisaldehyde using sodium triacetoxyborohydride and dimethylamine hydrochloride.

Used Chemicals

• m-Anisaldehyde [A0478]
• Dimethylamine Hydrochloride
• Sodium Acetate [S0559]
• Acetic Acid [A2035]
• Sodium Triacetoxyborohydride (= NaBH(OAc)₃) [S0394]
• THF

Procedure

A solution of m-anisaldehyde (1.00 g, 7.34 mmol), dimethylamine hydrochloride (1.20 g, 14.7 mmol), sodium acetate (964 mg, 11.8 mmol) and acetic acid (253 µL, 4.41 mmol) in THF (30 mL) was stirred at 0 °C for 5 minutes and then sodium triacetoxyborohydride (3.42 g, 16.2 mmol) was added to the solution and stirred at room temperature for 1 hour. The reaction was quenched with sat. aq. NaHCO₃ and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate:hexane = 0:100 - 10:90) to give 1-(3-methoxyphenyl)-N,N-dimethylmethanamine as a colorless liquid (940 mg, 77% yield).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.

Analytical Data

1-(3-Methoxyphenyl)-N,N-dimethylmethanamine

¹H NMR (270 MHz, DMSO); δ 7.22 (t, J = 7.8 Hz, 1H), 6.86-6.79 (m, 3H), 3.73 (s, 3H), 3.34 (s, 2H), 2.13 (s, 6H).

Lead Reference

• Reductive amination of aldehydes and ketones by using sodium triacetoxyborohydride
  • A. F. Abdel-Magid, C. A. Maryanoff, K. G. Carson, Tetrahedron Lett. 1990, 31, 5595.