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Triethylamine → 1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine

HRID 2460
Notes
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Reaction equation

HRID 2460 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].C(N(CC)CC)C>C(Cl)Cl>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1)[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 196900081-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidineYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Fluorobenzoyl)piperidine (207 mg, 1.0 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added bromoacetoaldehyde diethylacetal (305 mg, 1.5 mmol) and triethylamine (0.5 ml). After 12 hours of heating under reflux, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 81 mg (25.0%) of the title compound in the form of orange oil.

Workup

  1. temperatureAfter 12 hours of heating
  2. temperatureunder reflux
  3. customthe solvent was removed by evaporation
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-3ff4585334ae4e29b75a677785e6dfac
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728835

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes