Hydrochloric Acid → HCID 21397145, compound

HRID 1439365Notes

Reaction equation

HRID 1439365 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH2:20])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:31](Cl)=[O:32].Cl>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[NH:20][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:36]([Cl:37])=[C:28]([Cl:27])[CH:29]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 21397136HCID 21397136, compound

Product 1

HCID 21397145HCID 21397145, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred suspension of 1-[3-(4-methyl-1-piperazinyl)propyl]-2-aminobenzimidazole (123 g., 0.45 mole) and anhydrous potassium carbonate (182 g., 1.35 mole), in methylene chloride (110 ml.) under nitrogen at 0° C. (ice-salt bath), was added 3,4-dichlorobenzoylchloride (113 g., 0.54 mole) at a rate sufficient to maintain the reaction temperature at 0°-3° C. The total time required for the addition was 1 hour. After stirring for 5 hours at ambient temperature, the reaction mixture was cooled to 10° C. and adjusted to pH 2 by the addition of 1N HCl. The precipitated hydrochloride salt was collected by suction filtration and then partitioned between 10% aqueous NaOH (800 ml.) and chloroform (1000 ml.). The phases were separated and the basic aqueous layer was extracted with chloroform (500 ml.). The organic layers were combined, dried (MgSo4), and evaporated in vacuo giving 1-[3-(4-methyl-1 -piperazinyl)propyl]-2-(3,4-dichlorobenzamido)benzimidazole as a pale yellow solid, m.p. 170°-172° C. Treatment with 2 equivalents of methane sulfonic acid in chloroform (500 ml.), removal of solvent and recrystallization from 1-propanol gave 136 g., (47% yield) of 1-[3-(4-methyl-1-piperazinyl)propyl]-2-(3,4-dichlorobenzamido) benzimidazole dimesylate as a white crystalline solid, m.p. 170°-173° C.

Workup

  1. temperatureto maintain the reaction temperature at 0°-3° C
  2. additionThe total time required for the addition
  3. temperaturethe reaction mixture was cooled to 10° C.
  4. filtrationThe precipitated hydrochloride salt was collected by suction filtration
  5. custompartitioned between 10% aqueous NaOH (800 ml.) and chloroform (1000 ml.)
  6. customThe phases were separated
  7. extractionthe basic aqueous layer was extracted with chloroform (500 ml.)
  8. customdried (MgSo4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-afe517513c284af59c5b22c3b6f26c0b
Source dataset
uspto-grants-1977_11
Patent number
US04059584

Reaction notes

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