Urea → HCID 67151381, compound

HRID 2064238Notes

Reaction equation

HRID 2064238 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-5d7cfa3f9f034f9d8d8f3bf21c39f1a2
Source dataset
uspto-grants-2012_10
Patent number
US08288405B2

Reaction notes

Loading…