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Triethylamine → ethyl 4-[[1-(2-phenylethyl)-1H-imidazol-2-yl]carbonyl]-1-piperidinecarboxylate

HRID 129460
Notes
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Reaction equation

HRID 129460 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:22]([CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)=[O:23].[OH-].[Na+]>C(#N)C.N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:22]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]2)=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 102196211-PhenethylimidazoleHCID 11096122Ethyl 4-(chlorocarbonyl)-1-piperidinecarboxylate

Product 1

HCID 19371512ethyl 4-[[1-(2-phenylethyl)-1H-imidazol-2-yl]carbonyl]-1-piperidinecarboxylateYield 34%

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
HCID 6342AcetonitrileSolvent

Procedure

To a cooled mixture of 54.2 g of 1-(2-phenylethyl)-1H-imidazole, 34.7 g of N,N-diethylethanamine and 50 ml of pyridine there were added dropwise 69.2 g of ethyl 4-chlorocarbonyl-1-piperidinecarboxylate(temp.≤0.20° C.) and then 30 ml of acetonitrile. The whole was stirred for 2 hours at room temperature and for 4 hours at reflux temperature. After cooling, there were added 30 ml NaOH 50% and refluxing was continued for 1/2 hour. The cooled reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3). The eluent of the desired fraction was evaporated and the residue was dried, yielding 38 g (33.9%) of ethyl 4-[[1-(2-phenylethyl)-1H-imidazol-2-yl]carbonyl]-1-piperidinecarboxylate (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. temperaturerefluxing
  4. waitwas continued for 1/2 hour
  5. customThe cooled reaction mixture
  6. customwas evaporated
  7. extractionThe product was extracted with dichloromethane
  8. customthe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3)
  12. customThe eluent of the desired fraction was evaporated
  13. customthe residue was dried

Sources & evidence

ORD record
ord-4cab03c1a2de4a1c8f313f80627aff41
Source dataset
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05468743

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes