Potassium Iodide → HCID 14013226, compound

HRID 2309639Notes

Reaction equation

HRID 2309639 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CN(C)C=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][NH:34][C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:30][CH2:31]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 14518041HCID 14518041, compound

Product 1

HCID 14013226HCID 14013226, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.7 parts of 2-chloropyrimidine, 5.5 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidineethanamine, 2.12 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred overnight at 60°-70° 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) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 2.6 parts (40%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-2-pyrimidinamine; mp. 125.1° C. (374).

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) saturated with ammonia
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 1,1'-oxybisethane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-caf75098ace548b2b114afe534f92e57
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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