Acetic Acid → HCID 65323538, compound

To a stirred solution of 2-bromo-5-methoxybenzaldehyde (1 eq) in dichloroethane was added 3-aminopropanol (1.5 eq) followed by NaBH(OAc)3 (2 eq) and acetic acid (4 eq) and the resulting mixture was stirred at RT under nitrogen for 8 h. The reaction mixture was quenched by careful addition of 2M Na2CO3 solution and stirred 1 h. The mixture was concentrated in vacuo and poured into diethyl ether. The phases were separated and the organic phase washed with 1N HCl solution. The aqueous phase was then washed with diethyl ether and subsequently basified with 1N NaOH solution. The aqueous phase was extracted with diethyl ether, dried over Na2SO4 and concentrated in vacuo to give 3-(((2-bromo-5-methoxyphenyl)methyl) amino)propan-1-ol as a clear oil. EI-MS m/z 274, 276 (M+H)+

1. customThe reaction mixture was quenched by careful addition of 2M Na2CO3 solution
2. stirringstirred 1 h
3. concentrationThe mixture was concentrated in vacuo
4. additionpoured into diethyl ether
5. customThe phases were separated
6. washthe organic phase washed with 1N HCl solution
7. washThe aqueous phase was then washed with diethyl ether
8. extractionThe aqueous phase was extracted with diethyl ether
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-7ae482e6e0e04e13a1762c205aaff465

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06514964B1