Hydrochloric Acid → HCID 86754159, compound

HRID 580891Notes

Reaction equation

HRID 580891 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=N.[ClH:22].N([O-])=O.[Na+].[OH-].[Na+]>O>[CH3:1][C:2]([CH3:21])([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][N:5]=[C:6]([Cl:22])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178454580HCID 178454580, compound

Product 1

HCID 86754159HCID 86754159, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution containing 2.23 g (7.63 mmoles) of N-(2,2-dimethyl-3-piperidinopropoxy)-3-pyridinecarboxamidine in 30 ml of a 1:1 mixture of concentrated hydrochloric acid and water, 2.63 g (38.2 mmoles) of sodium nitrite dissolved in 10 ml of water are dropwise added at 0° C. The reaction mixture is stirred at the same temperature for an additional 2 hours, then the pH value is adjusted to 12 by adding 2N sodium hydroxide solution, and the mixture is extracted twice with 30 ml of chloroform each. The organic phase is washed with 30 ml of water, dried over sodium sulfate, filtered and evaporated. The oily residue (1.83 g) is purified by column chromatography to give the title compound as a pale yellow oil in a yield of 1.62 g (68.5%).

Workup

  1. additionare dropwise added at 0° C
  2. extractionthe mixture is extracted twice with 30 ml of chloroform each
  3. washThe organic phase is washed with 30 ml of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue (1.83 g) is purified by column chromatography

Sources & evidence

ORD record
ord-b837eaa01339412488b61da201285736
Source dataset
uspto-grants-1999_07
Patent number
US05919796

Reaction notes

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