Piperidine → HCID 23503256, compound

HRID 1835168Notes

Reaction equation

HRID 1835168 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.N1CCCCC1>CO>[Cl:11][C:12]1[CH:13]=[C:14]([CH2:15][C:6]2[S:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[C:2]=2[OH:1])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Product 1

HCID 23503256HCID 23503256, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-oxotetrahydrothiophene-3-carboxylate (18.5 g) and 3-chlorobenzaldehyde (48.5 g) were heated at 100° C. with piperidine (4 ml) for 15 minutes and then allowed to cool to room temperature. The resulting yellow solid was stirred in methanol (300 ml) for 18 hours and collected. The yellow solid was suspended in ethanol (300 m) and dichloromethane (200 ml), para-toluenesulfonic acid(10 g) was added and the suspension was heated at reflux for 48 hours. The reaction mixture was allowed to cool and was then concentrated. The residue was purified by chromatography, eluting with 10:1 isohexane:dichloromethane, to give the sub-title compound (22.32 g).

Workup

  1. customcollected
  2. additiondichloromethane (200 ml), para-toluenesulfonic acid(10 g) was added
  3. temperaturethe suspension was heated
  4. temperatureat reflux for 48 hours
  5. temperatureto cool
  6. concentrationwas then concentrated
  7. customThe residue was purified by chromatography
  8. washeluting with 10:1 isohexane

Sources & evidence

ORD record
ord-781c8ade3f104064ba6b7647e83e8149
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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