Ethyl 4-amino-1-piperidinecarboxylate → (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine

HRID 323183

Reaction equation

[CH2:1]([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]1Cl)[CH3:2].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1>C(OCC)(=O)C.CCCCCC>[CH2:1]([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[NH:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22]1)[CH3:2]

Participants

Conditions

Temperature: 170 °C

Procedure

Combine 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole (3.06 g, 13.62 mmol) and ethyl 4-aminopiperidine-1-carboxylate (5.16 g, 30 mmol) and heat to 150° C. After 12 hours, heat to 170° C. After 8 hours, cool the reaction mixture and partition between dichloromethane (150 mL) and water. Separate the layers and extract the organic layer with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/1 to give (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine: Rf=0.15 (silica gel, ethyl acetate/hexane).

Workup

waitAfter 8 hours
temperaturecool the reaction mixture
custompartition between dichloromethane (150 mL) and water
customSeparate the layers
extractionextract the organic layer with water
dry with materialDry the organic layer over Na2SO4
filtrationfilter
customevaporate in vacuo
customto give a residue

Sources & evidence

ORD record: ord-f5b1e0492c1340f09d2a6f9c5b78700a
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Linked notes

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