Urea → HCID 67151381, compound

HRID 2404261Notes

Reaction equation

HRID 2404261 reaction equation
N([O-])=O.[Na+].[N:5]1([C:11]([C:13]2[N:18]=[CH:17][C:16](N)=[CH:15][CH:14]=2)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.NC(N)=O.[I-:24].[Na+]>Cl>[I:24][C:16]1[CH:15]=[CH:14][C:13]([C:11]([N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:12])=[N:18][CH:17]=1

Participants

6

Reactant 4

HCID 1176UreaHCID 5238Sodium IodideHCID 23668193Sodium NitriteHCID 671512211301214-66-3

Product 1

HCID 67151381HCID 67151381, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of sodium nitrite (69 g) in concentrated hydrochloric acid (1.5 L) was added to crude 6-(piperidin-1-ylcarbonyl)pyridin-3-amine at 0 C, and the mixture was stirred for 10 minutes. Urea (20 g) was added, and the mixture was stirred for 15 minutes. Sodium iodide (150 g) was added, and the product was separated by filtration and recrystallized from ethanol to give 5-iodo-2-(piperidin-1-ylcarbonyl)pyridine (yield 23% calculated for methyl 5-nitropyridine-2-carboxylate, 71 g).

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customthe product was separated by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-348d570b441240efa64b9cf01036cc9c
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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