Benzaldehyde → 3-(Benzylamino)propanol

To a solution of benzaldehyde (10 g, 94.23 mmol) and trimethylorthoformate (15.5 mL, 141 mmol ) in MeOH (300 mL) was added dropwise 3-amino-1-propanol (7.21 mL, 94.23 mmol) at room temperature. The reaction was allowed to stir at room temperature for 5 hours followed by cooling to 0° C. in an ice bath. Sodium borohydride (3.56 g, 94.23 mmol) was added in two portions and when the bubbling stopped the solvent was evaporated. The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL). The aqueous layer was extracted twice with ethyl acetate (75 mL). The ethyl acetate extracts were collected and washed twice with Brine (50 mL), dried over MgSO4, filtered, and concentrated. Drying afforded 14.42 g (93%) of the compound which was used in the next step of synthesis without further purification.

1. temperatureby cooling to 0° C. in an ice bath
2. customwas evaporated
3. customThe resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL)
4. extractionThe aqueous layer was extracted twice with ethyl acetate (75 mL)
5. customThe ethyl acetate extracts were collected
6. washwashed twice with Brine (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customDrying

ORD record

ord-7fa5e51da58b467f9361341b0b1b717c

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559303B1