Hydrochloric Acid → 2,4-Dimethylphenol

BBr3 (2 ml of 1M solution in DCM, 2.0 mmol) is added to a solution of benzyl-ethyl-{1-[1-(3-methoxy-2,6-dimethyl-phenyl)-isoquinolin-4-yl]-butyl}-amine (95 mg, 0.21 mmol) in DCM (8 ml) at −78° C. The mixture is allowed to warm to room temperature slowly, and after 2h, the mixture is cooled to 0° C. MeOH (1 ml) and 1N—HCl (20 uL) are added carefully. After heating for 10 min at 80° C., the mixture is cooled and then basified with 1N—NaOH to pH 10. The resulting mixture is extracted with DCM and the combined extracts are washed with saturated brine. Drying over Na2SO4, and removal of the solvent in vacuo gave a yellow residue that is purified by PTLC affording 19 mg of 3-{4-[1-benzyl-ethyl-amino)-butyl]-isoquinolin-1-yl}-2,4-dimethyl-phenol as a white solid.

1. temperatureAfter heating for 10 min at 80° C.
2. temperaturethe mixture is cooled
3. extractionThe resulting mixture is extracted with DCM
4. washthe combined extracts are washed with saturated brine
5. dry with materialDrying over Na2SO4, and removal of the solvent in vacuo
6. customgave a yellow residue that
7. customis purified by PTLC

ORD record

ord-c648773859da4646979eabbaa8f00ebd

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915288B2