1,2-Dichloroethane → HCID 18415938, compound

HRID 991009Notes

Reaction equation

HRID 991009 reaction equation
[NH:1]1[C:5]2[C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[S:8][C:4]=2[C:3]([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[N:2]1.[N:21]1([CH2:26][CH2:27][CH2:28][NH2:29])[CH:25]=[CH:24][N:23]=[CH:22]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[Cl:53]CCCl>C(O)C.Cl>[ClH:53].[ClH:53].[ClH:53].[NH:1]1[C:5]2[C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[S:8][C:4]=2[C:3]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:29][CH2:28][CH2:27][CH2:26][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[CH:15][CH:14]=2)=[N:2]1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 787361H-Imidazole-1-propanamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 9925621HCID 9925621, compound

Product 1

HCID 18415938HCID 18415938, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(1H-[1]benzothieno[3,2-c]pyrazol-3-yl)benzaldehyde (0.1 g 0.36 mmol), 3-(imidazol-1-yl)propylamine (0.058 g, 0.47 mmol) and glacial acetic acid (0.03 ml, 0.47 mmol) in 1,2-dichloroethane was stirred at room temp for about 1 hr. Solid sodium triacetoxyborohydride (0.084 g, 0.4 mmol) was then added in one portion and the resulting mixture stirred for about 16 hrs at room temp. An additional portion of sodium triacetoxyborohydride (0.084 g, 0.4 mmol) was added and the mixture stirred for another 24 hrs. The reaction mixture was poured onto a solution of saturated sodium bicarbonate (20 ml) and stirred for about 30 mins, the layers separated and the aqueous layer extracted with dichloromethane (2×50 ml). The combined extracts and organic layer were washed with water (1×25 ml), dried (MgSO4), filtered and concentrated in vacuo to give a waxy solid which was taken up in ethanol. Two drops of hydrochloric acid (conc) were added, the solution cooled and scratched to give a solid which was removed by filtration, dried in vacuo to give 4-(1H-[1]benzothieno[3,2-c]pyrazol-3-yl)-N-[3-(imidazol-1-yl)propyl]benzylamine trihydrochloride (0.09 g, 50%) Mpt 206-208° C.

Workup

  1. stirringthe mixture stirred for another 24 hrs
  2. stirringstirred for about 30 mins
  3. customthe layers separated
  4. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
  5. washThe combined extracts and organic layer were washed with water (1×25 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a waxy solid which
  10. temperaturethe solution cooled
  11. customto give a solid which
  12. customwas removed by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-2df5be96972b41898c88a236cf50a3ec
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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