Formaldehyde → 5-(2-Piperidinomethylpropionyl)-3-phenylisoxazole

HRID 1613872Notes

Reaction equation

HRID 1613872 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)(=[O:4])[CH2:2][CH3:3].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[CH2:22]=O>C(O)C>[N:16]1([CH2:3][CH:2]([CH3:22])[C:1]([C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=2)=[O:4])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 151807665-Propionyl-3-phenylisoxazole

Product 1

HCID 152278165-(2-Piperidinomethylpropionyl)-3-phenylisoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added to 10 ml of ethyl alcohol were 2.0 g (10.0 mmol) of 5-propiony-3-phenylisoxazole and 1.7 g (20.0 mmol) of piperidine, followed by the dropwise addition of 1.63 ml (20.0 mmol) of a 37% aqueous solution of formaldehyde under ice cooling. After the reaction mixture was stirred for 2 hours at room temperature, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl ether. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, whereby the target compound, namely, 5-(2-piperidinomethylpropionyl)-3-phenylisoxazole was obtained as crystals.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, whereby the target compound

Sources & evidence

ORD record
ord-64c6837c7545443e8adac51e118aeb57
Source dataset
uspto-grants-1993_03
Patent number
US05194606

Reaction notes

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