Formaldehyde → 3-{2-(1-Pyrrolidinylmethyl)-butyryl}-1,2-benzisoxazole

HRID 1450662Notes

Reaction equation

HRID 1450662 reaction equation
[C:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].C=O.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[C:22](=O)([O-])O.[Na+]>C(OCC)(=O)C.C(O)C>[N:17]1([CH2:22][CH:2]([CH2:3][CH3:4])[C:1]([C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][N:7]=2)=[O:5])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 199769213-Butyryl-1,2-benzisoxazole

Product 1

HCID 199769433-{2-(1-Pyrrolidinylmethyl)-butyryl}-1,2-benzisoxazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Added to 10 ml of ethanol were 1.55 g (8.2 mmol) of 3-butyryl-l,2-benzisoxazole prepared above in the procedure (1), 0.52 ml (9.9 mmol) of a 37% aqueous solution of formaldehyde and 0.82 ml (9.8 mmol) of pyrrolidine. The resultant mixture was heated under reflux for 3 hours. After cooling, the solvent was distilled off. The residue thus obtained was added to 50 ml of ethyl acetate, followed by extraction with 50 ml of dilute hydrochloric acid. A water layer thus obtained was alkalinized with an aqueous solution of sodium hydrogencarbonate, followed by extraction with 50 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then distilled off, whereby 3-{2-(-pyrroIidinylmethyl)-butyryl}-1,2-benzisoxazole was obtained as oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customThe residue thus obtained
  5. extractionfollowed by extraction with 50 ml of dilute hydrochloric acid
  6. customA water layer thus obtained
  7. extractionfollowed by extraction with 50 ml of ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-a8dc8918894440bba94f7d912d3c6f2e
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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