Hydrochloric Acid → 4,5,6,7-Tetrahydro-1H-benzo(d)imidazole-5-carboxylic acid hydrochloride

HRID 1489145Notes

Reaction equation

HRID 1489145 reaction equation
N1([C:10]([CH:12]2[CH2:20][CH2:19][C:15]3[N:16]=[CH:17][NH:18][C:14]=3[CH2:13]2)=[O:11])C2C(=CC=CC=2)CC1.[OH-:21].[Na+].[ClH:23]>O>[ClH:23].[N:16]1[C:15]2[CH2:19][CH2:20][CH:12]([C:10]([OH:11])=[O:21])[CH2:13][C:14]=2[NH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1329642,3-dihydroindol-1-yl(4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanone

Product 1

HCID 532310384,5,6,7-Tetrahydro-1H-benzo(d)imidazole-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 24 g portion of the above mentioned (-)-5-(2,3-dihydroindol-1-yl)carbonyl-4,5,6,7-tetrahydrobenzimidazole was dissolved in 120 ml of 6N hydrochloric acid and heated under reflux for 3 hours. The reaction solution was evaporated to dryness under reduced pressure to obtain a residue which was then dissolved in water, made alkaline with an aqueous sodium hydroxide solution, and washed with ethyl ether. Subsequent acidification of the aqueous layer with hydrochloric acid and concentration under reduced pressure yielded a white powder of (+)-4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid hydrochloride containing NaCl.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction solution was evaporated to dryness under reduced pressure
  4. customto obtain a residue which
  5. washwashed with ethyl ether
  6. concentrationSubsequent acidification of the aqueous layer with hydrochloric acid and concentration under reduced pressure

Sources & evidence

ORD record
ord-03918802d4944a27bd9ae0fb3930178a
Source dataset
uspto-grants-1997_10
Patent number
US05677326

Reaction notes

Loading…