Hydrochloric Acid → HCID 21330741, compound

HRID 1391214Notes

Reaction equation

HRID 1391214 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.[OH-].[Na+].[CH:13](=O)[CH:14]([CH3:16])[CH3:15].Cl>O.CO>[ClH:1].[ClH:1].[CH:14]([CH:16]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1)([CH3:15])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 178478691HCID 178478691, compound

Product 1

HCID 21330741HCID 21330741, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 20 g of histamine dihydrochloride in 54 ml of water and 440 ml of methanol, 19.6 g of sodium hydroxide dissolved in 54 ml of water and 25 ml of isobutyraldehyde are added and the solution refluxed for 24 h. The solution is then acidified with 200 ml of conc. hydrochloric acid and evaporated in vacuo. The residue is taken up in methanol. The methanolic extract is evaporated in vacuo to give 23 g of 4-isopropyl-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine dihydrochloride, m.p. 238°, from which the free base, m.p. 112°, is obtained by ion-exchange on Amberlite (Trade Mark) IRA 410. A solution of 1.3 g of the base in 10 ml of dioxane is treated with 1.3 g of methyl isothiocyanate and refluxed for 4 h. The solution is cooled and filtered; 1.4 g of 4-isopropyl-5-(N-methyl-thiocarbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine, m.p. 240°, are collected.

Workup

  1. temperaturethe solution refluxed for 24 h
  2. customevaporated in vacuo
  3. extractionThe methanolic extract
  4. customis evaporated in vacuo

Sources & evidence

ORD record
ord-fabf587bbdab455f8826fa76dbb15505
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

Loading…