Hydrochloric Acid → 3-{[(4-Methoxyphenyl)methyl]amino}propan-1-ol

To a solution of 3-amino-propan-1-ol (15.0 g, 200 mmol) in methanol (300 ml) was added para-methoxybenzaldehyde (28.6 g, 210 mmol) and a few drops of acetic acid at room temperature. The mixture was stirred at room temperature for 2 hours and cooled to 0° C. After the addition of sodium borohydride (11.4 g, 300 mmol), the mixture was stirred at room temperature for another 2 hours and acidified with 3N hydrochloric acid. The biphasic mixture was stirred at room temperature for 10 minutes. The organic solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous phase was washed with ethyl acetate and basified with 6N sodium hydroxide. Extraction with chloroform was performed and the organic phase was dried over sodium sulfate followed by concentration in vacuo to afford 3-(4-methoxy-benzylamino)-propan-1-ol as pale yellow oil (16.4 g, 42%).

1. temperaturecooled to 0° C
2. stirringthe mixture was stirred at room temperature for another 2 hours
3. stirringThe biphasic mixture was stirred at room temperature for 10 minutes
4. customThe organic solvent was evaporated under reduced pressure
5. customthe residue was partitioned between water and ethyl acetate
6. washThe aqueous phase was washed with ethyl acetate and basified with 6N sodium hydroxide
7. extractionExtraction with chloroform
8. dry with materialthe organic phase was dried over sodium sulfate
9. concentrationfollowed by concentration in vacuo

ORD record

ord-6a886eccc8d344bd925a7d6489568f0f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108957B2