Hydrochloric Acid → N,N'-Dimethyl-N-(5-methyl-3-pyridyl)ethane-1,2-diamine dihydrochloride

HRID 631824Notes

Reaction equation

HRID 631824 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]([CH3:20])[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)C(=O)OC(C)(C)C.[ClH:21]>C(Cl)Cl>[ClH:21].[ClH:21].[CH3:20][N:12]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:11][CH2:10][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735429tert-Butyl N-methyl-N-[2-[methyl-(5-methyl-3-pyridyl)amino]ethyl]carbamate

Product 1

HCID 89825869N,N'-Dimethyl-N-(5-methyl-3-pyridyl)ethane-1,2-diamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-methyl-N-[2-[methyl-(5-methyl-3-pyridyl)amino]ethyl]carbamate (301 mg, 1.078 mmol) was dissolved in DCM (40 ml). Hydrochloric acid (4M in dioxane, 5.4 ml) was added and the mixture was stirred at room temperature for 48 hours. The mixture was concentrated under reduced pressure, diethylether was added and the mixture was stirred at room temperature for 4 days. The solids were collected by filtration, rinsed with diethylether and dried under reduced pressure to yield 199 mg (0.789 mmol, 73%) MS(ESI) m/z=180.2 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, diethylether
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 4 days
  4. filtrationThe solids were collected by filtration
  5. washrinsed with diethylether
  6. customdried under reduced pressure
  7. customto yield 199 mg (0.789 mmol, 73%) MS(ESI) m/z=180.2 [M+1]+

Sources & evidence

ORD record
ord-82ca38c6695d4dd8a0c6239fa6d85901
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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