Hydrochloric Acid → 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Temperature

25 °C

HCl (939 mg, 4.9 mmol), HOBT (660 mg, 4.9 mmol) and DIPEA (2.2 ml, 12.69 mmol) were added to a solution of the product just obtained in step 4 (1 g, 3.2 mmol) in THF (20 ml). The reaction mixture was stirred at 25° C. for 30 min, a solution of 3-pyridin-4-yl-3,9-diaza-spiro[5.5]undecane (3.2 mmol, 1 eq.) in THF (20 ml) was then added and the mixture was stirred further at 25° C. for 12 h. The reaction mixture was diluted with methylene chloride and washed with sat. NH4Cl solution and NaHCO3 solution. The organic phase was washed with water and sat. NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography.

1. stirringthe mixture was stirred further at 25° C. for 12 h
2. washwashed with sat. NH4Cl solution and NaHCO3 solution
3. washThe organic phase was washed with water and sat. NaCl solution
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by column chromatography

ORD record

ord-f40fde89c1794236ab5d8f649bd0b912

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2