Sodium Carbonate → 2-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazole

HRID 979946Notes

Reaction equation

HRID 979946 reaction equation
ClCCN.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH:22]C2CCN(CCN=C=S)CC2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH2:22])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 133692-ChloroethylamineHCID 12891753HCID 12891753, compound

Product 1

HCID 30193052-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.2 parts of 2-chloroethanamine, 4.1 parts of 1-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 2.2 parts of sodium carbonate and 135 parts of tetrahydrofuran was stirred for 3 hours at room temperature. The mixture was heated to reflux and stirring was continued overnight at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized twice from acetonitrile, yielding 1 part of N-[1-[2-[4,5-dihydro-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine; mp. 147.6° C. (compound 99).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. stirringstirring
  4. waitwas continued overnight
  5. temperatureat reflux temperature
  6. filtrationThe reaction mixture was filtered
  7. customthe filtrate was evaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized twice from acetonitrile

Sources & evidence

ORD record
ord-055dc952ecdd4fffae65ae84adc722a2
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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