Hydrochloric Acid → N-Methyl-1-[5-phenyl-1-(2-thienylsulfonyl)-1H-pyrrol-3-yl]methanamine hydrochloride

5-Phenyl-1-(2-thienylsulfonyl)-1H-pyrrole-3-carbaldehyde (180 mg) was dissolved in methanol (20 mL), a 40% methylamine methanol solution (220 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (64 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (20 mL) was added, and the mixture was stirred for 5 min. The reaction mixture was alkalized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:4→0:1), and dissolved in ethyl acetate (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 171 mg, 82%).

1. stirringthe mixture was stirred for 10 min
2. stirringthe mixture was stirred for 5 min
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:4→0:1)
8. dissolutiondissolved in ethyl acetate (5 mL)
9. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
10. concentrationthe mixture was concentrated under reduced pressure
11. customThe residue was crystallized from ethyl acetate

ORD record

ord-4795bb3b3ef548dfb1431bba67631bbc

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048909B2