Water → (4E)-N-Methyl-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine Hemigalactarate

To a solution of (4E)-N-methyl-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine (151.4 mg, 0.68 mmol) in absolute ethanol (2.3 mL) was added galactaric acid (72.2 mg, 0.34 mmol). Water (0.5 mL) was added dropwise while gently warming the light-brown solution. The solution was filtered through glass wool to remove a few insoluble particles, washing the filter plug with ethanol-water (4:1, v/v) (1 mL). The filtrate was diluted with ethanol (3.4 mL), cooled to ambient temperature, and further cooled at 5° C. for 18 h. Because no precipitate had formed, the solution was concentrated on a rotary evaporator. The resulting solids were dried under high vacuum and recrystallized from 2-propanol-water. After cooling at 5° C. for 48 h the product was filtered, washed with cold 2-propanol, and vacuum dried at 45° C. for 6 h. Further vacuum drying at ambient temperature for 18 h afforded 168 mg (76.1%) of a white to off-white powder, mp 141-143.5° C.

1. temperaturewhile gently warming the light-brown solution
2. filtrationThe solution was filtered through glass wool
3. customto remove a few insoluble particles
4. washwashing the filter plug with ethanol-water (4:1
5. additionThe filtrate was diluted with ethanol (3.4 mL)
6. temperaturefurther cooled at 5° C. for 18 h
7. customBecause no precipitate had formed
8. concentrationthe solution was concentrated on a rotary evaporator
9. customThe resulting solids were dried under high vacuum
10. customrecrystallized from 2-propanol-water
11. temperatureAfter cooling at 5° C. for 48 h the product
12. filtrationwas filtered
13. washwashed with cold 2-propanol, and vacuum
14. customdried at 45° C. for 6 h
15. customFurther vacuum drying at ambient temperature for 18 h
16. customafforded 168 mg (76.1%) of a white to off-white powder, mp 141-143.5° C.

ORD record

ord-36eb5dee23784ca7b351803c2a33bec3

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288420B2