Ammonia → HCID 13056042, compound

HRID 2198755Notes

Reaction equation

HRID 2198755 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:2]1.Cl[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23](C(C)=C)[C:22]1=[O:33].C(=O)(O)[O-].[Na+].N>O1CCCC1.CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22]3=[O:33])[CH2:12][CH2:11]2)=[CH:2]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 130168791-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 13056042HCID 13056042, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture consisting of 3.0 gm of 4-(3-indolyl)-piperidine, 4.0 gm of 1-(4-chloro-butyl)-3-isopropenylbenzimidazolone, 1.3 gm of sodium bicarbonate, 30 ml of dimethyl-formamide and 30 ml of tetrahydrofuran was refluxed for 16 hours. Thereafter, the reaction mixture was poured into a mixture of ice and ammonia, the aqueous mixture was extracted with ethyl acetate, and the extract solution was washed with water, dried and evaporated to dryness in vacuo. The residue was dissolved in ether, etheric hydrogen chloride was added to the solution, and the precipitate formed thereby was collected by filtration, dried and dissolved in 100 ml of ethanol. The resulting solution was cooled, 16 ml of concentrated sulfuric acid were carefully added while stirring, and the mixture was allowed to stand at 20° C. for two hours, whereupon it was poured into a mixture of ice and ammonia. The precipitate formed thereby was collected by filtration and recrystallized from ethanol, yielding 3.2 gm (55% of theory) of the compound of the formula ##STR13## having a melting point of 196° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. washthe extract solution was washed with water
  4. customdried
  5. customevaporated to dryness in vacuo
  6. dissolutionThe residue was dissolved in ether
  7. additionetheric hydrogen chloride was added to the solution
  8. customthe precipitate formed
  9. filtrationthereby was collected by filtration
  10. customdried
  11. dissolutiondissolved in 100 ml of ethanol
  12. temperatureThe resulting solution was cooled
  13. addition16 ml of concentrated sulfuric acid were carefully added
  14. additionwas poured into a mixture of ice and ammonia
  15. customThe precipitate formed
  16. filtrationthereby was collected by filtration
  17. customrecrystallized from ethanol
  18. customyielding 3.2 gm (55% of theory) of the compound of the formula

Sources & evidence

ORD record
ord-3cd6460e83eb40b191b9c1cbccb2648e
Source dataset
uspto-grants-1982_11
Patent number
US04359468

Reaction notes

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