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

HRID 345181Notes

Reaction equation

HRID 345181 reaction equation
[C:1]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[CH2:23]=O>C(O)C>[N:17]1([CH2:23][CH:2]([CH2:3][CH3:4])[C:1]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:7]=2)=[O:5])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 101306023-Phenyl-5-butyrylisoxazole

Product 1

HCID 117587775-(2-Piperidinomethylbutyryl)-3-phenylisoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added to 320 ml of ethyl alcohol were 160 g (0.74 mol) of 5-butyryl-3-phenylisoxazole and 103 ml of piperidine, followed by the dropwise addition of 96 ml (1.18 mol) of a 37% aqueous solution of formaldehyde under ice cooling over 30 minutes. After the reaction mixture was stirred for 1.5 hours at room temperature, the solvent was distilled off. The residue was dissolved in 800 ml of ethyl ether. The resultant solution was washed with water and the organic layer then dried over anhydrous magnesium sulfate. The solvent was distilled off, whereby the target compound, 5-(2-piperidinomethylbutyryl)-3-phenylisoxazole was obtained as colorless crystals.

Workup

  1. distillationthe solvent was distilled off
  2. dissolutionThe residue was dissolved in 800 ml of ethyl ether
  3. washThe resultant solution was washed with water
  4. dry with materialthe organic layer then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8c8eb7812bf2476eb31316d2f9faf258
Source dataset
uspto-grants-1991_10
Patent number
US05055585

Reaction notes

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