Water → HCID 14207549, compound

Temperature

25 °C

Isonicotinoyl chloride hydrochloride (1.44 g, 8.09 mmol) was stirred in dry dichloromethane (20 ml) and triethylamine (4.0 ml, 2.9 g, 20 mmol) was added. The mixture was stirred at 25° C. for 5-10 minutes, then cooled in an ice bath. 1-Amino-3-phenyl-2-propanone hydrochloride (1.00 g, 5.39 mmol) was added in portions over 4 minutes. The reaction was stirred 0.5 hour while warming to 25° C., then 0.5 hour at 25° C. Water (5-10 ml) was added and the mixture was stirred 5 minutes before being extracted with ethyl acetate (75 ml). The organic layer was washed with saturated aqueous sodium bicabonate (2×35 ml) and saturated aqueous sodium chloride (35 ml), dried (sodium sulfate), decanted, and evaporated. The residue was purified by flash column chromatography on silica gel (50 g) eluted with 5% isopropanol in dichloromethane, yielding N-(3-phenyl-2-oxopropyl)isonicotinamide (1.23 g, 89% yield) as an orange oil which crystallized (m.p. 85°-86° C.) upon standing. Recrystallization of a portion of this material from toluene raised the m.p. to 86°-88° C.

1. temperaturecooled in an ice bath
2. stirringThe reaction was stirred 0.5 hour
3. temperaturewhile warming to 25° C.
4. custom0.5 hour
5. customat 25° C
6. stirringthe mixture was stirred 5 minutes
7. extractionbefore being extracted with ethyl acetate (75 ml)
8. washThe organic layer was washed with saturated aqueous sodium bicabonate (2×35 ml) and saturated aqueous sodium chloride (35 ml)
9. dry with materialdried (sodium sulfate)
10. customdecanted
11. customevaporated
12. customThe residue was purified by flash column chromatography on silica gel (50 g)
13. washeluted with 5% isopropanol in dichloromethane

ORD record

ord-fa7f4c5a44c24854b7fa0fc150dc068e

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04746669