Dimethylformamide → Ethyl 5-(4-ethylphenyl)1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylate

HRID 1642813Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15](OC3C=CC([N+]([O-])=O)=CC=3)=[O:16])[CH2:12][CH:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[OH:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:36]3[CH2:37][CH2:38][CH:33]([OH:32])[CH2:34][CH2:35]3)=[O:16])[CH2:12][CH:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

370 mg (0.81 mmol) of 3-ethyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate, 245 mg (2.42 mmol) of 4-hydroxypiperidine and 112 mg (0.81 mmol) of potassium carbonate were added to 9 ml of DMF and heated in a single-mode microwave (Emrys Optimizer) at 150° C. for 15 min. For work-up, water was added and the reaction solution was extracted with ethyl acetate. The organic phase was dried with sodium sulphate and concentrated under reduced pressure. The residue was purified by preparative HPLC. Yield: 208 mg (66% of theory)

Workup

extractionthe reaction solution was extracted with ethyl acetate
dry with materialThe organic phase was dried with sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-8f0ae3ddae6f4931bb418d4dde41c6d3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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