Ethylenediamine → HCID 2299525, compound

To a magnetically stirred, ambient temperature solution of 2-(3-bromo-phenoxy)-ethanol (3.6 g, 16.7 mmol) and N-methylmorpholine [109-02-4] (2.2 mL, 20.0 mmol) in ethyl acetate (200 mL) was added methanesulfonyl chloride [124-63-0] (1.3 mL, 16.8 mmol). The reaction was stirred over night then washed with brine and the phase separated ethyl acetate extract dried (MgSO4) and added to a stirred ambient temperature solution of ethylenediamine [107-15-3] (33.3 mL, 497.0 mmol) in ethyl acetate (300 mL) from a pressure equalizing addition funnel over the course of 15 minutes. The addition funnel was replaced with a condenser and the reaction refluxed for 4 h then cooled and washed with brine. The ethyl acetate phase was dried (CaSO4) and evaporated to obtain N1-(2-(3-bromophenoxy)ethyl)ethane-1,2-diamine as 4.7 g of clear yellow liquid. LRMS (ESI) m/z 259.1/261.1 [(M+H)]+, calc'd for C10H15BrN2O: 259.15.

1. washthen washed with brine
2. customthe phase separated ethyl acetate
3. extractionextract
4. dry with materialdried (MgSO4)
5. additionaddition funnel over the course of 15 minutes
6. customThe addition funnel was replaced with a condenser
7. temperaturethe reaction refluxed for 4 h
8. temperaturethen cooled
9. washwashed with brine
10. dry with materialThe ethyl acetate phase was dried (CaSO4)
11. customevaporated

ORD record

ord-bb933cb0888b4180842eb4bd13014b84

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969565B2