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

HRID 728828Notes

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

Participants

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

temperatureCool the reaction mixture to room temperature
customremove the solvents in vacuo
customThe resulting oil is chromatographed on alumina (activity III)
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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