Hydrochloric Acid → 6-[(2-Aminoethyl)amino]nicotinonitrile dihydrochloride

HRID 2088642Notes

Reaction equation

HRID 2088642 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=1)(C)(C)C.[ClH:20]>O1CCOCC1>[ClH:20].[ClH:20].[NH2:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 47453716tert-Butyl (2-((5-cyanopyridin-2-yl)amino)ethyl)carbamate

Product 1

HCID 669113296-[(2-Aminoethyl)amino]nicotinonitrile dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.9 g (30 mmol) of tert-butyl{2-[(5-cyanopyridin-2-yl)amino]ethyl}carbamate (Example 1A) were dissolved in 100 ml of 4 N hydrogen chloride in dioxane and stirred for 30 min. The reaction mixture was concentrated to half of its original volume and the same amount of diethyl ether was added. The reaction mixture was stirred for 20 min, and the product was filtered off and washed with diethyl ether. This gave 7 g (94% of theory) of the product as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated to half of its original volume
  2. additionthe same amount of diethyl ether was added
  3. stirringThe reaction mixture was stirred for 20 min
  4. filtrationthe product was filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-dc6abe669cc744ba8a8f337e3514d6a3
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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