Lithium Hydroxide → 1-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(carboxy methoxy ethyl)-4-piperidinyl]methanone

HRID 1769033Notes

Reaction equation

[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][C:27]([O:29]C)=[O:28])[CH2:19][CH2:18]1)=[O:16].[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C.O>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:19][CH2:18]1)=[O:16]

Participants

Conditions

Temperature: 60 °C

Procedure

Dissolve 1-[[(2-ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(carbomethoxy methoxy ethyl)-4-piperidinyl]methanone (0.9 g, 2.15 mmol) in tetrahydrofuran/water (20 mL, 1/1). Add lithium hydroxide monohydroate (932 mg, 8.5 mmol). Seal the flask and warm to 60° C. for 3 hours. Dilute with ethyl acetate/water, acidify and separate the organic phase. Dry (MgSO4), evaporate the solvent in vacuo, and purify by ion-exchange chromatography to give the title compound.

Workup

customSeal the flask
customseparate the organic phase
dry with materialDry (MgSO4)
customevaporate the solvent in vacuo
custompurify by ion-exchange chromatography

Sources & evidence

ORD record: ord-17e85e41d4a7487383df2cb29d9ad0a1
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380731

Reaction notes

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