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Sodium Hydroxide → N-[2-[[2-Hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl]amino]ethyl]-4-(1H-imidazol-1-yl)benzamide

HRID 728828
Notes
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Reaction equation

HRID 728828 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:9][CH:8]=1.[OH-:19].[Na+].O1C(C[C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][O:33][CH3:34])=[CH:27][CH:26]=2)C1>CO.O>[OH:19][CH:7]([CH2:6][O:18][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][O:33][CH3:34])=[CH:29][CH:30]=1)[CH2:8][NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 45259278N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide hydrochlorideHCID 536452031,2-Epoxy-3-[4-(2-methoxyethyl)phenyl]propane

Product 1

HCID 14739880N-[2-[[2-Hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl]amino]ethyl]-4-(1H-imidazol-1-yl)benzamide

Reagents, catalysts & solvents 2

HCID 887Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 10 g (37.5 mmol) N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide hydrochloride in 50 mL methanol and 5 mL water with 1.69 g (42 mmol) sodium hydroxide, add 8.59 g(41.2 mmol) 1,2-epoxy-3-[4-(2-methoxyethyl)phenyl]propane. Heat the mixtureto 60° C. for about 18 h. Cool the reaction mixture to room temperature and remove the solvents in vacuo. The resulting oil is chromatographed on alumina (activity III) using CH2Cl2 :MeOH, 98:2. Combine the appropriate fractions and remove the solvents to give the title compound which can be recrystallized from ethyl acetate.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. customremove the solvents in vacuo
  3. customThe resulting oil is chromatographed on alumina (activity III)
  4. customCombine the appropriate fractions and remove the solvents

Sources & evidence

ORD record
ord-b14908542a7148cc8aedf22e03f96318
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05051423

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes