Propionic Acid → N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

To a stirred brown solution of 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (318 mg, 1.4 mmol) and propionic acid (114 mg, 1.54 mmol) in CH2Cl2 (7.0 mL) at 0° C. under argon was added EDCI (63.3 mg, 0.330 mmol). Stirring was continued overnight and the reaction mixture was allowed to warm up to room temperature. The reaction mixture was poured onto aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution; the combined organic phases were dried over Na2SO4, filtered and evaporated. The residue was dissolved in CH2Cl2, evaporated with n-pentane (3×) to ca. 10 ml each time, while the product precipitated; then, the solvent was decanted and the residue washed twice with n-pentane to afford the title compound (0.365 g, 92%) as light brown solid. MS: 283.0 (M+H+, 1Br).

1. extractionfollowed by extraction with AcOEt (3×)
2. washThe organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution
3. dry with materialthe combined organic phases were dried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. dissolutionThe residue was dissolved in CH2Cl2
7. customevaporated with n-pentane (3×) to ca. 10 ml each time, while the product
8. customprecipitated
9. customthen, the solvent was decanted
10. washthe residue washed twice with n-pentane

ORD record

ord-07d4dbf302264553bbb2ccd3b0197313

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133158B2