Hydrochloric Acid → 5-(3-Phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazole

HRID 1585220Notes

Reaction equation

HRID 1585220 reaction equation
Cl.[N:2]1[C:6]2[CH2:7][CH2:8][CH:9]([C:11]([OH:13])=O)[CH2:10][C:5]=2[NH:4][CH:3]=1.[C:14]1([CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:14]1([CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([C:11]([CH:9]3[CH2:8][CH2:7][C:6]4[N:2]=[CH:3][NH:4][C:5]=4[CH2:10]3)=[O:13])[CH2:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 109323533-phenyl-2,3-dihydro-1H-indoleHCID 110301834,5,6,7-Tetrahydro-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 98410295-(3-Phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazoleYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixed solution of 518 mg of hydrochloride (racemic form) of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid, 500mg of (+)-3-phenylindoline, and 15 ml of dimethyl formamide was cooled to 0° C. The cooled solution and 736 mg of hydrochloride of N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide added thereto were gradually heated to normal room temperature and stirred at the same temperature for 12 hours. The resultant reaction solution was concentrated under a reduced pressure. The residue of this concentration was neutralized by addition of an aqueous potassium carbonate solution and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and then distilled. The residue of this distillation was refined by silica gel column chromatography to obtain 725 mg of 5-(3-phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazole (82.5%) as an epimer mixture.

Workup

  1. customThe resultant reaction solution
  2. concentrationwas concentrated under a reduced pressure
  3. concentrationThe residue of this concentration
  4. additionwas neutralized by addition of an aqueous potassium carbonate solution
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. distillationThe residue of this distillation

Sources & evidence

ORD record
ord-3cae8705a75a425c82f7c09c94afe287
Source dataset
uspto-grants-1999_08
Patent number
US05936098

Reaction notes

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