Hydrochloric Acid → 4-{3-Hydroxy-1-[(methylamino)methyl]propyl}benzonitrile

tert-Butyl {2-(4-cyanophenyl)-4-[(triisopropylsilyl)oxy]butyl}methylcarbamate (0.37 g) was dissolved in THF (8 mL) at 0° C. Hydrochloric acid (8 ml of 6M solution) was added and the mixture stirred overnight at room temperature. The volatiles were removed by evaporation and then removed azeotropically after the addition of methanol (5×50 mL). The residue was dissolved in water and the solution alkalised to pH 8-9 by the addition of Na2CO3 (s) and then extracted thrice with ethyl acetate (100 mL). The organic solution was dried over Na2SO4 and then the solvent was evaporated. The product was purified by flash chromatography (CH2Cl2-MeOH—NH4OH, 9:1:0.1). There was obtained 0.10 g, 60%) of 4-{3-Hydroxy-1-[(methylamino)methyl]propyl}benzonitrile as a solid. 1H NMR (300 MHz, CDCl3): 1.9-2.0 (m, 2H), 2.5 (s, 3H), 2.8-2.9 (m, 3H), 3.4-3.7 (m, 3H), 3.7 (m, 1H), 7.3 (d, 2H), 7.6 (d, 2H); LCMS: m/z 205 (M+1)+.

1. customThe volatiles were removed by evaporation
2. customremoved azeotropically
3. additionafter the addition of methanol (5×50 mL)
4. dissolutionThe residue was dissolved in water
5. additionthe solution alkalised to pH 8-9 by the addition of Na2CO3 (s)
6. extractionextracted thrice with ethyl acetate (100 mL)
7. dry with materialThe organic solution was dried over Na2SO4
8. customthe solvent was evaporated
9. customThe product was purified by flash chromatography (CH2Cl2-MeOH—NH4OH, 9:1:0.1)

ORD record

ord-7660577f674a4e23b20266e2c09274fb

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402581B2