Acetic Acid → Benzenemethanamine, N-cyclohexyl-

To a stirred solution of cyclohexylamine (9.34 g) in methanol (300 ml) was added benzaldehyde (10.0 g) followed by activated 3 Å molecular sieves. After 1 h, sodium cyanoborohydride (7.13 g) was added followed by the dropwise addition of acetic acid (9.2 ml), and the reaction was stirred overnight. The reaction mixture was filtered through hiflo, the solvent removed in vacuo and the resulting white solid was heated under reflux in 5M potassium hydroxide solution for 30 mins. The product was extracted into dichloromethane (3×100 ml) and the combined organic layers were washed with brine (100 ml), dried over sodium sulphate and the solvent was removed in vacuo to give a clear oil. The product was purified by column chromatography (eluting with ethyl acetate) then distillation; bpt=137° C. at 1.0 mbarr. 1H NMR (360 MHz, D6 -DMSO) δ0.94-1.24 (5H, m), 1.48-1.88 (5H, m), 2.32 (1H, m), 2.32 (1H, m), 3.10 (2H, s(b)), 3.72 (2H, s), 7.14-7.40 (5H, m).

1. filtrationThe reaction mixture was filtered through hiflo
2. customthe solvent removed in vacuo
3. temperaturethe resulting white solid was heated
4. temperatureunder reflux in 5M potassium hydroxide solution for 30 mins
5. extractionThe product was extracted into dichloromethane (3×100 ml)
6. washthe combined organic layers were washed with brine (100 ml)
7. dry with materialdried over sodium sulphate
8. customthe solvent was removed in vacuo
9. customto give a clear oil
10. customThe product was purified by column chromatography (eluting with ethyl acetate)
11. distillationdistillation

ORD record

ord-3d3945a9f0564dd4b627cc1c751dfe06

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05618812