N-Hydroxyphthalimide → O-[2-(Morpholin-4-yl)ethyl]hydroxylamine

To a solution of 2-morpholinoethanol (5 g, 38 mmol) in CH2Cl2 (250 mL) was added 2-hydroxyisoindoline-1,3-dione (9.3 g, 57 mmol) and triphenylphosphine (15 g, 57 mmol). The resultant mixture was cooled to 0° C. and diisopropyl azodicarboxylate (11 ml, 57 mmol) was slowly added drop wise with an addition funnel under N2 atmosphere. The reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was concentrated to provide clear oil, which was purified by flash chromatography (50% EtOAc—Hexane). The resultant clear oily compound was dissolved in CH2Cl2 (50 ml). Hydrazine hydrate (5.8 mL, 76 mmol) was added. The reaction mixture was stirred at ambient temperature for 8 h. The resultant solid was filtered off and the filtrate concentrated under reduced pressure to provide a clear oil of O-(2-morpholinoethyl)hydroxylamine (3.5 g, 24 mmol). [M+H] calc'd for C6H14N2O2, 147; found, 147.

1. concentrationThe reaction mixture was concentrated
2. customto provide clear oil, which
3. customwas purified by flash chromatography (50% EtOAc—Hexane)
4. dissolutionThe resultant clear oily compound was dissolved in CH2Cl2 (50 ml)
5. stirringThe reaction mixture was stirred at ambient temperature for 8 h
6. filtrationThe resultant solid was filtered off
7. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-4a173523e38d4bdb8ea1ba8ead234aab

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618290B2