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

HRID 345180Notes

Reaction equation

HRID 345180 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-propionyl-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-4e207a65436b45e18fb44158e76e4887
Source dataset
uspto-grants-1991_10
Patent number
US05055585

Reaction notes

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