Sodium Carbonate → 2-Aminobenzimidazole

HRID 2166126Notes

Reaction equation

HRID 2166126 reaction equation
ClCCOCC.Br.Br.N1CCC([NH:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)CC1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[NH:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH2:15]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 31374DimethylacetamideHCID 22036968N-(Piperidin-4-yl)-1H-benzo[d]imidazol-2-amine dihydrobromide

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 32 parts of 1-chloro-2-ethoxyethane, 94.5parts of N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 90 parts of sodium carbonate and 540 parts of N,N-dimethylacetamide was stirred overnight at 70° C. After cooling, the reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was boiled in acetonitrile. After cooling, the precipitated product was filtered off and dried, yielding 42.4 parts (58.8%) of N-[1-(2-ethoxyethyl)-4-piperidinyl[-1H-benzimidazol-2-amine; mp. 212° C. (interm. 29).

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. temperatureAfter cooling
  7. filtrationthe precipitated product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-a2dada330cdf4c488f3c7bb0c55e1fe3
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

Loading…