Sodium Hydroxide → (3-Nitro-benzyl)dipropylamine

Commercially available 3-nitrobenzylamine hydrochloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.62 g) was suspended in chloroform (15 ml) and then added with a 1 mol/l sodium hydroxide aqueous solution (15 ml). The aqueous layer was extracted with chloroform and the extract was then dried with anhydrous magnesium sulfate, followed by distilling the solvent off. Subsequently, the residue was dissolved in anhydrous methanol (25 ml) and then added with propionaldehyde (1.49 ml), trimethyl orthoformate (2.82 ml), and sodium cyanoborohydride (1.62 g), followed by stirring at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off. Then, the residue was added with water and extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (608.1 mg) as a yellow oily substance.

1. extractionThe aqueous layer was extracted with chloroform
2. dry with materialthe extract was then dried with anhydrous magnesium sulfate
3. distillationby distilling the solvent off
4. dissolutionSubsequently, the residue was dissolved in anhydrous methanol (25 ml)
5. additionadded with propionaldehyde (1.49 ml), trimethyl orthoformate (2.82 ml), and sodium cyanoborohydride (1.62 g)
6. customAfter completion of the reaction
7. distillationthe solvent was distilled off
8. additionThen, the residue was added with water
9. extractionextracted with chloroform
10. dry with materialThe extract was dried with anhydrous magnesium sulfate
11. distillationthe solvent was then distilled off
12. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-6dcf40d79a714721b00a127add180b52

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176227B2