Sodium Carbonate → HCID 178433270, compound

HRID 979928Notes

Reaction equation

HRID 979928 reaction equation
Cl.Cl[CH2:3][C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH3:9].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH:25][CH:26]1[CH2:27][CH2:28][N:29]([CH2:3][C:4]2[NH:8][CH:7]=[N:6][C:5]=2[CH3:9])[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 135879951-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amineHCID 178433265HCID 178433265, compound

Product 1

HCID 178433270HCID 178433270, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.4 parts of 5-(chloromethyl)-4-methyl-1H-imidazole monohydrochloride, 6 parts of 1-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 4.25 parts of sodium carbonate and 135 parts of N,N-dimethylformamide was stirred and heated for 3 hours at 70° C. The reaction mixture was poured onto water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of acetonitrile and methanol, yielding 4.7 parts (60.2%) of 1-(2-furanylmethyl)-N-[1-[(4-methyl-1H-imidazol-5-yl)methyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 242.1° C. (compound 1).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from a mixture of acetonitrile and methanol

Sources & evidence

ORD record
ord-2a73bbde20974649b7506ceaa3b5686c
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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