Tetrahydrofuran → 4-(Piperidine-1-carbonyl)benzaldehyde

HRID 1577804Notes

Reaction equation

HRID 1577804 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.O1CCCC1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O>[N:17]1([C:1]([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)=[O:3])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 120884-Formylbenzoic acid

Product 1

HCID 190690894-(Piperidine-1-carbonyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.0 g. of 4-carboxybenzaldehyde, 13.6 g. of N,N'-carbonyldiimidazole and 100 ml. of tetrahydrofuran is allowed to stand for one hour, then 9.4 ml. of piperidine is added. The reaction mixture is allowed to stand for 18 hours, then heated at reflux temperature for one hour. Water is added and the solvent is distilled off. Methylene chloride is added and the solution is washed with 25 ml. of concentrated hydrochloric acid, then with water then is dried over magnesium sulfate. The mother liquor is concentrated to yield p-piperidinocarbonylbenzaldehyde as an oil.

Workup

  1. additionA mixture of 12.0 g
  2. waitto stand for 18 hours
  3. temperatureheated
  4. temperatureat reflux temperature for one hour
  5. distillationthe solvent is distilled off
  6. additionMethylene chloride is added
  7. washthe solution is washed with 25 ml
  8. dry with materialof concentrated hydrochloric acid, then with water then is dried over magnesium sulfate
  9. concentrationThe mother liquor is concentrated

Sources & evidence

ORD record
ord-bd9a6f5629644c45b662a9611e1fceaf
Source dataset
uspto-grants-1981_09
Patent number
US04289769

Reaction notes

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