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CHEMBRDG-BB 4004844 synthesis

2synthesis methods
-

Yield: 0.354 g (20.1%)

Reaction Conditions:

with sodium chloride in methanol

Steps:

10 3-(3-Pyridyloxy)propylamine
3-(3-Pyridyloxy)propylamine The 3-chloro-1-(3-pyridyloxy)propane (1.98 g, 11.6 mmol) was dissolved in methanol (25 mL) and added to concentrated ammonium hydroxide solution (29.7%, 14.8 M, 55 mL) in a heavy-walled glass pressure-tube apparatus. The tube was sealed and the mixture was stirred and heated at 100° C. (oil bath temperature) for 6 h. After cooling, the mixture was concentrated by rotary evaporation. Saturated NaCl solution (10 mL) was added to the residue, and the solution (pH 6) was extracted with ether (3*25 mL) to remove impurities. The aqueous layer was basified to pH 10 with 10% NaOH solution, and the mixture was extracted with chloroform (4*25 mL). The combined chloroform extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 0.354 g (20.1%) of an oil.

References:

DULL, GARY MAURICE;WAGNER, JARED MILLER;HADIMANI, SRISHAIKUMAR BASAWANNAPPA;CONSILVIO, MICHAEL B. US2001/14691, 2001, A1