Water → HCID 13588075, compound

HRID 845779Notes

Reaction equation

HRID 845779 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1C=CC(C([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[NH:23][CH:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]#[N:32])[CH2:26][CH2:25]2)=O)=C1.O.[OH-].[Na+]>O1CCCC1>[NH2:32][CH2:31][CH2:30][N:27]1[CH2:26][CH2:25][CH:24]([NH:23][C:15]2[NH:14][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15614722HCID 15614722, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13588075HCID 13588075, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 180 parts of tetrahydrofuran were added carefully 2.4 parts of lithium aluminium hydride under nitrogen atmosphere. Then there was added dropwise a solution of 7 parts of 4-[[1-(3-furanylcarbonyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile in tetrahydrofuran: temp. rose to 50° C. Upon completion, stirring was continued overnight at reflux temperature. The reaction mixture was cooled in an ice-bath and decomposed by the successive additions of 3 parts of water, 9 parts of a sodium hydroxide solution 15% and 9 parts of water. The whole was filtered over Hyflo and the filtrate was evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (80:20 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 3.6 parts (69.5%) of N-[1-(2-aminoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 99.8° C. (intermediate 129).

Workup

  1. customrose to 50° C
  2. temperatureat reflux temperature
  3. temperatureThe reaction mixture was cooled in an ice-bath
  4. filtrationThe whole was filtered over Hyflo
  5. customthe filtrate was evaporated
  6. filtrationThe residue was purified by filtration over silica gel using
  7. additiona mixture of trichloromethane and methanol (80:20 by volume) saturated with ammonia
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-5b463de678f3469c99876a1ae71e1f95
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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