Benzoyl chloride → HCID 14013098, compound

HRID 1904864Notes

Reaction equation

HRID 1904864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]3C=[CH:32][CH:31]=[CH:30][N:29]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.C([N:36](CC)CC)C.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]([C:28]3[N:29]=[CH:30][CH:31]=[CH:32][N:36]=3)[C:41](=[O:48])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14013291HCID 14013291, compound

Product 1

HCID 14013098HCID 14013098, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled mixture of 6.2 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-2-pyridinamine, 2 parts of N,N-diethylethanamine and 90 parts of tetrahydrofuran was added dropwise slowly a solution of 1.9 parts of benzoyl chloride in 45 parts of tetrahydrofuran. Upon completion, stirring was continued for 2 hours. The reaction mixture was evaporated. Water was added to the residue. The solution was treated with ammonium hydroxide. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 5.3 parts (69%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-N-(2-pyrimidinyl)benzamide; mp. 108.1° C. (508).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customThe reaction mixture was evaporated
  4. additionWater was added to the residue
  5. additionThe solution was treated with ammonium hydroxide
  6. extractionThe product was extracted with 4-methyl-2-pentanone
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-c84cb185633f4287832b5bb810c459bb
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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