Sodium Iodide → 1-(2-furanylmethyl)-N-[1-[2-(2-thiazolylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

HRID 979931Notes

Reaction equation

HRID 979931 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:21]([CH2:22][C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>O.CN(C)C(=O)C>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][N:21]1[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[N:18]=[C:17]1[NH:16][CH:13]1[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][NH:7][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 13588039N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-furanylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 137696921-(2-furanylmethyl)-N-[1-[2-(2-thiazolylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.7 parts of 2-bromothiazole, 5.1 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-furanylmethyl)-1H-benzimidazol-2-amine, 5 parts of sodium carbonate, 0.1 parts of sodium iodide and 9 parts of N,N-dimethylacetamide was stirred for 3 hours at about 140° C. Water was added and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 3 parts of 1-(2-furanylmethyl)-N-[1-[2-(2-thiazolylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 153.1° C. (compound 48).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-68ba9a22b3a042d28c01c3e39418660c
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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