Hydrochloric Acid → HCID 131721293, compound

HRID 580889Notes

Reaction equation

HRID 580889 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=N)[CH3:2].[ClH:19].N([O-])=O.[Na+].[OH-].[Na+]>O>[ClH:19].[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][N:8]=[C:9]([Cl:19])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178464011HCID 178464011, compound

Product 1

HCID 131721293HCID 131721293, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

9.5 g (37.9 mmoles) of N-(3-diethylaminopropoxy)-3-pyridinecarboxamidine are added under stirring to the mixture of 65 ml of distilled water and 21.7 ml of concentrated hydrochloric acid, cooled to 0° C. To the yellow solution, 13.08 g (189.5 mmoles) of sodium nitrite dissolved in 54 ml of distilled water are dropwise added at -5° C. during 50 minutes, then the reaction mixture is stirred at a temperature of -5° C. for 2 hours. Subsequently, the pH of the solution is adjusted to 11 by adding 2N sodium hydroxide solution, and the mixture is extracted 3 times with 70 ml of chloroform each. The organic phase is washed with 30 ml of water, dried over sodium sulfate and evaporated. The residue is purified by column chromatography (adsorbent: Merck Kieselgel 60; eluent: chloroform/methanol 1:1). The base obtained in a yield of 5.17 g (50.6%) is transformed by adding methanolic solution of hydrogen chloride to obtain the title hydrochloride, m.p.: 152-153° C.

Workup

  1. additionare dropwise added at -5° C. during 50 minutes
  2. extractionthe mixture is extracted 3 times with 70 ml of chloroform each
  3. washThe organic phase is washed with 30 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is purified by column chromatography (adsorbent: Merck Kieselgel 60; eluent: chloroform/methanol 1:1)
  7. customThe base obtained in a yield of 5.17 g (50.6%)

Sources & evidence

ORD record
ord-22a0e17aa0e748018fa065b1259f5b34
Source dataset
uspto-grants-1999_07
Patent number
US05919796

Reaction notes

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