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Add ethylene diamine (200 mL, 3000 mmol) and toluene (1200 mL) to a 3 L flask and cool to <5° C. Add a solution of 3-(4-Nitro-phenyl)-propionaldehyde (63 g, 280 mmol) in toluene (300 mL) via addition funnel over 45 minutes with vigorous stirring. Remove the cooling bath and heat to reflux to remove water by azeotropic distillation (Dean Stark trap). Concentrate the reaction under reduced pressure to an oil. Dilute the crude oil with methanol (450 mL) and cool to 0° C. Add sodium borohydride (13 g, 340 mmol) in 1-2 g portions with stirring, holding the temperature below 5° C. Stir the reaction for 20 minutes at 5° C. and then allow the reaction to warm to room temperature and stir for an additional 30 minutes. Cool to <0° C. and add water and dichloromethane. Separate the layers and extract the aqueous layer with dichloromethane. Combine the organic layers and wash with brine and dry over MgSO4. Filter the slurry and concentrate under reduced pressure to a red oil (73 g). The title compound was used without purification. 1H NMR (CDCl3, 500.0 MHz): δ 8.12 (d, 2H, J=8 Hz), 7.32 (d, 2H, J=8 Hz), 2.74-2.81 (m, 4H), 2.61-2.67 (m, 4H), 1.84 (p, 2H, J=7.5 Hz), 1.57 (br s, 2H).

1. temperaturecool to <5° C
2. additionvia addition funnel over 45 minutes with vigorous stirring
3. customRemove the cooling bath
4. temperatureheat
5. temperatureto reflux
6. customto remove water
7. distillationby azeotropic distillation (Dean Stark trap)
8. concentrationConcentrate
9. customthe reaction under reduced pressure to an oil
10. customthe temperature below 5° C
11. customthe reaction for 20 minutes at 5° C.
12. customthe reaction
13. temperatureto warm to room temperature
14. stirringstir for an additional 30 minutes
15. temperatureCool to <0° C.
16. customSeparate the layers
17. extractionextract the aqueous layer with dichloromethane
18. washwash with brine
19. dry with materialdry over MgSO4
20. filtrationFilter the slurry
21. concentrationconcentrate under reduced pressure to a red oil (73 g)
22. customThe title compound was used without purification