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

HRID 1642813
Notes
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Reaction equation

HRID 1642813 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 580024743-Ethyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

Product 1

HCID 58002667Ethyl 5-(4-ethylphenyl)1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes