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Sodium Hydroxide → 4-({[4-(dipropylamino)butyl]amino}methyl)-N,N-bis(1H-imidazol-2-ylmethyl)benzamide

HRID 68629
Notes
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Reaction equation

HRID 68629 reaction equation
[CH2:1]([N:4]([CH2:48][CH2:49][CH3:50])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:47]=[CH:46][C:14]([C:15]([N:17]([CH2:32][C:33]2[N:34](COCC[Si](C)(C)C)[CH:35]=[CH:36][N:37]=2)[CH2:18][C:19]2[N:20](COCC[Si](C)(C)C)[CH:21]=[CH:22][N:23]=2)=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[OH-].[Na+]>CO.Cl>[CH2:48]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]([CH2:32][C:33]2[NH:34][CH:35]=[CH:36][N:37]=2)[CH2:18][C:19]2[NH:23][CH:22]=[CH:21][N:20]=2)=[O:16])=[CH:46][CH:47]=1)[CH2:49][CH3:50]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67163333HCID 67163333, compound

Product 1

HCID 116483934-({[4-(dipropylamino)butyl]amino}methyl)-N,N-bis(1H-imidazol-2-ylmethyl)benzamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound 9 in methanol (2 mL), concentrated hydrochloric acid (2 mL) was added. The reaction mixture was stirred at 80° C. for 5 hours. The reaction mixture was added by an aqueous 5N sodium hydroxide solution and then extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1→80:20:4) to obtain the title compound (21 mg) having the following physical properties.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1→80:20:4)

Sources & evidence

ORD record
ord-9db2b9dda76f4443b2bd526b2843f450
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822459B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes