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Sodium Hydroxide → 1H-Benzimidazole, 2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1-(2-(2-propynyloxy)ethyl)-, (E)-2-butenedioate (1:2)

HRID 1388160
Notes
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Reaction equation

HRID 1388160 reaction equation
Cl[C:2]1[N:6]([CH2:7][CH2:8][O:9][CH2:10][C:11]#[CH:12])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[CH3:17][N:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH2:10]([O:9][CH2:8][CH2:7][N:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=[C:2]1[N:21]1[CH2:22][CH2:23][CH2:24][N:18]([CH3:17])[CH2:19][CH2:20]1)[C:11]#[CH:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2283491-MethylhomopiperazineHCID 444972Fumaric AcidHCID 15585274HCID 15585274, compound

Product 1

HCID 64484211H-Benzimidazole, 2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1-(2-(2-propynyloxy)ethyl)-, (E)-2-butenedioate (1:2)Yield 60.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-1-[2-(propargyloxy)ethyl]-benzimidazole (3.70 g) and N-methylhomopiperazine (9.00 g) is stirred at 120° C. for 5 hours. A 5% aqueous sodium hydroxide (50 ml) is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and then concentrated. The residue is dissolved in a small amount of chloroform and subjected to column chromatography using silica gel (60 g), and then eluted with chloroform-methanol (10:1 by volume). The eluate is concentrated to give a pale yellow oily substance (1.90 g). The pale yellow oily substance is dissolved in ethanol (3 ml) and the solution is added to a solution of fumaric acid (1.50 g) in hot ethanol (18 ml). After the mixture is allowed to cool, the precipitated crystals are separated by filtration and recrystallized from ethyl acetate-ethanol to give 1-[2-(propargyloxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate (2.14 g) as colorless needles, m.p. 122°-124.5° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in a small amount of chloroform
  6. washeluted with chloroform-methanol (10:1 by volume)
  7. concentrationThe eluate is concentrated
  8. customto give a pale yellow oily substance (1.90 g)
  9. temperatureto cool
  10. customthe precipitated crystals are separated by filtration
  11. customrecrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-f680df1797c54fc7913bdc24bacf960a
Source dataset
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04430343

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes