Sodium Hydroxide → 2-Aminobenzimidazole

HRID 477660Notes

Reaction equation

HRID 477660 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.FC1C=CC(CNC2C=NC=CC=2[N+]([O-])=O)=CC=1.S1C=CC=C1C[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41]C1CCN(CC#N)CC1.[OH-].[Na+]>O1CCCC1.O>[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[NH:34][C:33]=1[NH2:41]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 135880204-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrileHCID 15614715HCID 15614715, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 2.5 parts of lithium aluminum hydride and 225 parts of tetrahydrofuran was added dropwise a solution of 13 parts of 4-[[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile in tetrahydrofuran under nitrogen atmosphere. Upon completion, stirring was continued for 3 hours at reflux. The reaction mixture was cooled in an ice bath and decomposed by the successive additions of 2.5 parts of water, 7.5 parts of a sodium hydroxide solution 15% and 7.5 parts of water. The whole was filtered over Hyflo and the filtrate was evaporated. The residue was crystallized from acetonitrile, yielding 9.5 parts (72%) of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-thienylmethyl)-1e,uns/H/ -benzimidazol-2-amine; mp. 137.1° C. (intermediate 108).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. filtrationThe whole was filtered over Hyflo
  4. customthe filtrate was evaporated
  5. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-882f0e35b2dc4738af0637b0e3f563fd
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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