Hydrochloric Acid → 1-[2-(benzyloxy)ethyl]cyclopropan-1-amine

To a solution of 3-(benzyloxy)propanenitrile (16.9 g 105 mmol) in diethyl ether (400 mL) were added titanium isopropoxide (35.7 mL, 115 mmol) and ethyl magnesium bromide (210 mL, 1 M in diethyl ether) successively at room temperature. After being stirred for 0.5 hour, boron trifluoride etherate (27 mL, 525 mmol) was added. After stirring for another 0.5 hour, 10% aqueous solution of sodium hydroxide (ca. 5.5 mL) was introduced to the above mixture. The resulting mixture was acidified with 1N hydrochloric acid to pH 3, and then washed with dichloromethane. The aqueous layer was basified with 5% aqueous solution of sodium hydroxide to pH 8˜9 and extracted with dichloromethane (100 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford 11 g of 1-[2-(benzyloxy)ethyl]cyclopropanamine (yield was 55%).

1. stirringAfter stirring for another 0.5 hour
2. washwashed with dichloromethane
3. extractionextracted with dichloromethane (100 mL)
4. washThe organic layer was washed with brine (100 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-a07ff223039e448db639b5f94388f3f6

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871756B2