Butanal → HCID 4639791, compound

2-Phenethylamine (12.5 mL, 12.1 g, 99.5 mmol), butyraldehyde (13.2 mL, 10.8 g, 150 mmol), and 3 Å molecular sieves were stirred at 50 ° C. for 1 h, then at RT for 5.5 h. The reaction was then diluted with CH2Cl2, filtered through celite, then concentrated to an oil. That oil was dissolved in absolute EtOH (150 mL-previously cooled to 0 ° C.), and NaBH4 (5.7 g, 150 mmol) was added. The reaction was stirred at RT overnight, concentrated, partitioned between water and Et2O, then the organic layer was washed with water and brine. After drying over Na2SO4, filtration, and concentration, the compound was purified by vacuum distillation using a 6″ Vigeraux column (98-100° C./9 mm). Recovered 8.2 g (46%).

1. filtrationfiltered through celite
2. concentrationconcentrated to an oil
3. dissolutionThat oil was dissolved in absolute EtOH (150 mL-
4. additionwas added
5. concentrationconcentrated
6. custompartitioned between water and Et2O
7. washthe organic layer was washed with water and brine
8. dry with materialAfter drying over Na2SO4, filtration, and concentration
9. distillationthe compound was purified by vacuum distillation
10. customVigeraux column (98-100° C./9 mm)
11. customRecovered 8.2 g (46%)

ORD record

ord-35b8198a731143e285a4305be2e2cd7b

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310095B1