Hydrochloric Acid → HCID 178457905, compound

HRID 1391221Notes

Reaction equation

HRID 1391221 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[N:3]=[CH:2]1.[CH:10]([N:13]=[C:14]=[O:15])([CH3:12])[CH3:11].Cl>O1CCOCC1.C(O)(C)C>[CH:10]([NH:13][C:14]([N:6]1[CH2:7][CH2:8][C:9]2[NH:1][CH:2]=[N:3][C:4]=2[CH2:5]1)=[O:15])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61277Isopropyl isocyanateHCID 178420865HCID 178420865, compound

Product 1

HCID 178457905HCID 178457905, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.46 g of 4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine and 6.8 g of isopropyl isocyanate in 50 ml of dry dioxane is refluxed for 2 h. After evaporation to dryness, the residue is dissolved in 25 ml of methanol and treated with 12.5 ml of 2N sodium hydroxide for 2 h at room temperature. After neutralization, the solution is extracted with chloroform. Evaporation of the solvent leaves a residue (2.21 g, oil) that is treated with one equivalent of hydrogen chloride in isopropanol. After cooling, 1.7 g of 5-(N-isopropyl-carbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine hydrochloride, m.p. 190°, are collected.

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe residue is dissolved in 25 ml of methanol
  3. additiontreated with 12.5 ml of 2N sodium hydroxide for 2 h at room temperature
  4. extractionAfter neutralization, the solution is extracted with chloroform
  5. customEvaporation of the solvent
  6. customleaves a residue (2.21 g, oil) that
  7. temperatureAfter cooling
  8. custom1.7 g of 5-(N-isopropyl-carbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine hydrochloride, m.p. 190°, are collected

Sources & evidence

ORD record
ord-e4bd1b518f74440db1439b1f95fb3655
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

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