Water → HCID 9794140, compound

Temperature

120 °C

An Ace Glass pressure tube (185 mL) was charged with 3-chloro-1-(3-pyridyloxy)propane (0.762 g, 4.437 mmol), cyclopropylamine (8.24 g, 194.3 mmol), water (20 mL) and methanol (20 mL). The resulting light-brown solution was heated at 120° C. (oil bath temperature) for 2.5 h and allowed to cool to ambient temperature over 16 h. The solution was concentrated by rotary evaporation to an oily residue that was diluted with saturated NaCl solution (25 mL). The mixture was acidified to pH 1.0 with 10% HCl solution and extracted with CHC3 (2×35 mL) to remove impurities. The aqueous phase was basified to pH 6 with 100% NaOH solution and extracted (4×25 mL) to remove other impurities. The aqueous phase was basified to pH 10 with 100% NaOH solution and extracted with CHCl3 (4×50 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, concentrated (rotary evaporator) and briefly dried under high vacuum to give 0.250 g of a brown oil. The oil was purified by column chromatography on silica gel (20 g) eluting with CHCl3—CH3OH (100:2) to remove impurities, followed by CHCl3—CH3OH—Et3N (50:50:2) to remove the product. Selected fractions were combined to give 220 mg (25.8%) of a brown semi-solid.

1. temperatureto cool to ambient temperature over 16 h
2. concentrationThe solution was concentrated by rotary evaporation to an oily residue that
3. additionwas diluted with saturated NaCl solution (25 mL)
4. extractionextracted with CHC3 (2×35 mL)
5. customto remove impurities
6. extractionextracted (4×25 mL)
7. customto remove other impurities
8. extractionextracted with CHCl3 (4×50 mL)
9. dry with materialThe combined CHCl3 extracts were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. custom(rotary evaporator)
13. custombriefly dried under high vacuum

ORD record

ord-6d945b193e944054a0d58db88e5d442b

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441006B2