4-Fluorobenzoyl chloride → 4-fluorobenzoyl-N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-[1,4'-bipiperidine]-4-amine

HRID 280340Notes

Reaction equation

HRID 280340 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[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>ClCCl>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([CH:23]2[CH2:24][CH:19]([NH:18][C:10]3[N:9]([CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[N:11]=3)[CH2:20][CH2:21][N:22]2[CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:37])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 15614720N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl][1,4'-bipiperidine]-4-amine

Product 1

HCID 1317146754-fluorobenzoyl-N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-[1,4'-bipiperidine]-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 4 parts of N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-[1,4'-bipiperidine]-4-amine, 1 part ofN,N-diethylethanamine and 91 parts of dichloromethane was added dropwise a solution of 1.6 parts of 4-fluorobenzoyl chloride in 39 parts of dichloromethane: slightly exothermic reaction, the temperature rises from 25° C. to 30° C. Upon completion, stirring was continued for one hour at room temperature. The reaction mixture was purified by high performance liquid chromatography using a mixture of trichloromethane, hexane and methanol (45:45:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 1.8 parts (34%) of 1'-(4-fluorobenzoyl-N-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-[1,4'-bipiperidine]-4-amine; mp. 194.3° C.; (compound 18).

Workup

  1. customslightly exothermic reaction
  2. customrises from 25° C. to 30° C
  3. customThe reaction mixture was purified by high performance liquid chromatography
  4. additiona mixture of trichloromethane, hexane and methanol (45:45:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-5f67845e48674dbf9393e00abb40e112
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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