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

Temperature

25 °C

HCl (503 mg, 2.62 mmol), HOBT (177 mg, 1.311 mmol) and DIPEA (0.6 ml) were added to a solution of the product just obtained in step 5 (400 mg, 1.3114 mmol) in methylene chloride (10 ml). The reaction mixture was stirred at 25° C. for 30 min and then cooled to 0° C. and 3-pyridin-4-yl-3,9-diaza-spiro[5.5]undecane (364 mg, 1.57 mmol) was added. The reaction mixture was stirred at 25° C. for 12 h, subsequently diluted with methylene chloride and washed with sat. NH4Cl solution and with 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. temperaturecooled to 0° C.
2. stirringThe reaction mixture was stirred at 25° C. for 12 h
3. washwashed with sat. NH4Cl solution and with NaHCO3 solution
4. washThe organic phase was washed with water and sat. NaCl solution
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by column chromatography

ORD record

ord-9404062857804e3abbc800c0b6dc32e1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2