Acetic Acid → 1-(3-Morpholin-4-yl-phenyl)propylamine

Temperature

65 °C

A mixture of 1-(3-morpholin-4-yl-phenyl)propan-1-one (4.06 g, 18.5 mmol), powdered 3A molecular sieves (4 g), in ammonia (2.0 M solution in methanol) (61.2 mL) was stirred in sealed vessel at 65° C. for 2 hours, at which time sodium cyanoboronhydride (2.33 g, 37 mmol) and glacial acetic acid (8.47 mL) was added and the mixture was stirred at 65° C. for another 2 hours. After cooling down, the reaction mixture was filtered to remove molecular sieves and the filtrate was concentrated under vacuum. Solids was re-dissolved in dichloromethane (100 mL) and washed with saturated sodium bicarbonate solution (15 mL). The aqueous layer was extracted with dichloromethane (2×25 mL) and the combined organic layer was dried over magnesium sulfate, and concentrated under vacuum. The crude pale yellow oil was purified by Biotage flash chromatography with 90:10:10 dichloromethane:methanol:triethylamine to afford the title compound as a pale yellow clear oil (2.56 g).

1. additionwas added
2. temperatureAfter cooling down
3. filtrationthe reaction mixture was filtered
4. customto remove molecular sieves
5. concentrationthe filtrate was concentrated under vacuum
6. dissolutionSolids was re-dissolved in dichloromethane (100 mL)
7. washwashed with saturated sodium bicarbonate solution (15 mL)
8. extractionThe aqueous layer was extracted with dichloromethane (2×25 mL)
9. dry with materialthe combined organic layer was dried over magnesium sulfate
10. concentrationconcentrated under vacuum
11. customThe crude pale yellow oil was purified by Biotage flash chromatography with 90:10:10 dichloromethane

ORD record

ord-c0f4a2529e964cc1aad11b069d29e153

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831080B2