Acetic Acid → HCID 86722609, compound

Triethylamine (0.2 mL, 1.313 mmol) was added to 20 mL of 3-((3,4-dichlorophenyl)(phenoxy)methyl)azetidine hydrochloride (300 mg, 0.870 mmol) dissolved in a methanol solution, and the mixture was stirred at room temperature for 1 hour. 37% formaldehyde aqueous solution (0.3 ml, 3.50 mmol) and acetic acid (0.2 ml, 3.50 mmol) were added to the reaction mixture, and NaBH(OAc)3 (742 mg, 3.50 mmol) was added thereto, followed by stirring for one day. Thereafter, 1 mL of 1 N NaOH was added thereto, and the mixture was stirred for 30 minutes. The organic layer was washed with distilled water, and the organic layer was adjusted to pH 7 using a 1 N NaOH aqueous solution, and extracted with methylene chloride (3*30 mL) and dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain a colorless liquid, which was purified by flash chromatography (methylene chloride:methanol (9:1, v/v)). The product was identified as a single compound by TLC (methylene chloride:methanol (9:1, v/v)).

1. additionwas added
2. stirringby stirring for one day
3. stirringthe mixture was stirred for 30 minutes
4. washThe organic layer was washed with distilled water
5. extractionextracted with methylene chloride (3*30 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was removed by reduced pressure evaporation
8. customto obtain a colorless liquid, which
9. customwas purified by flash chromatography (methylene chloride:methanol (9:1

ORD record

ord-b7f84c681cae46b08c1c88296b9dc7f3

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120771B2