Ammonium fluoride → (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

HRID 323510

Reaction equation

[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1)(C(C)(C)C)(C)C.[F-].[NH4+].C(=O)(O)[O-].[Na+]>CO>[OH:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

Combine (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (0.53 g, 12 mmol) and ammonium fluoride (2.667 g, 72 mmol) in methanol (60 mL). Heat to about 60° C. After 2.5 hours, cool, evaporate in vacuo and partition the evaporated reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer twice with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine.

Workup

temperaturecool
customevaporate in vacuo
custompartition
customthe evaporated reaction mixture between dichloromethane
customSeparate the layers
extractionextract the organic layer twice with water
dry with materialDry the organic layer over MgSO4
filtrationfilter
customevaporate in vacuo

Sources & evidence

ORD record: ord-442278bd30b547888e969a8de56d3b47
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Linked notes

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