Hydrochloric Acid → N-Ethyl-N-(4-methyl-2-pyridyl)ethane-1,2-diamine dihydrochloride

HRID 631818Notes

Reaction equation

HRID 631818 reaction equation
[CH2:1]([N:3]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1)[CH2:4][CH2:5][NH:6]C(=O)OC(C)(C)C)[CH3:2].[ClH:21]>C(Cl)Cl>[ClH:21].[ClH:21].[CH2:1]([N:3]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1)[CH2:4][CH2:5][NH2:6])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735427Tert-butyl (2-(ethyl(4-methylpyridin-2-yl)amino)ethyl)carbamate

Product 1

HCID 89825614N-Ethyl-N-(4-methyl-2-pyridyl)ethane-1,2-diamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-[2-[ethyl-(4-methyl-2-pyridyl)amino]ethyl]carbamate (130 mg, 0.465 mmol) was dissolved in DCM (10 ml) and flushed with nitrogen. Hydrochloric acid (4N in dioxane, 9.31 mmol, 2.33 ml) was added and the mixture was stirred at room temperature overnight. The product was filtered off, dissolved in a mixture of acetonitrile and water and obtained by evaporation under reduced pressure to yield 58 mg (0.229 mmol, 49%) MS(ESI) m/z=180.2 [M+1]+.

Workup

  1. customflushed with nitrogen
  2. filtrationThe product was filtered off
  3. dissolutiondissolved in a mixture of acetonitrile and water
  4. customobtained by evaporation under reduced pressure
  5. customto yield 58 mg (0.229 mmol, 49%) MS(ESI) m/z=180.2 [M+1]+

Sources & evidence

ORD record
ord-1facea2468954d5ba911121b8d9e0120
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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