Potassium Iodide → 1-[3-{4-[(2-chlorophenyl)phenylmethyl]-1-piperazinyl}propyl]1H-benzimidazole trihydrochloride dihydrate

HRID 354983Notes

Reaction equation

HRID 354983 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.C(O)(=[O:16])C.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)([O-])[O-:39].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH2:16].[OH2:39].[ClH:1].[ClH:18].[ClH:1].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[N:26]1[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=[CH:6]2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 131055171-(3-Chloropropyl)-1H-benzimidazoleHCID 705345701-[(2-Chlorophenyl)phenylmethyl]piperazine acetate

Product 1

HCID 705350241-[3-{4-[(2-chlorophenyl)phenylmethyl]-1-piperazinyl}propyl]1H-benzimidazole trihydrochloride dihydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.9 parts of 1-(3-chloropropyl)-1H-benzimidazole, 7 parts of 1-[(2-chlorophenyl)phenylmethyl]piperazine acetate, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 20 hours with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol and 2,2'-oxybispropane. The salt is filtered off and crystallized from 2-propanol, yielding 1-[3-{4-[(2-chlorophenyl)phenylmethyl]-1-piperazinyl}propyl]-1H-benzimidazole trihydrochloride dihydrate; mp. 182.9° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-6d4cde76017b4b41a0b9325c0fc55f59
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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