2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin → 2-Aminomethyl-1,4-benzodioxane

HRID 374669

반응식

HRID 374669 반응식
Cl[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[K].C1(=O)[NH:18]C(=O)C2=CC=CC=C12>CN(C)C=O>[NH2:18][CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1

참가 물질

4

반응물 2

HCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxinHCID 24194345Phthalimide potassium salt

생성물 1

HCID 150532-Aminomethyl-1,4-benzodioxane

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Commercial grade of 2-chloromethyl-1,4-benzodioxane (10.0 g, 54.7 mmol) and phthalimide potassium salt (12.0 g, 65.0 mmol) were added to N,N-dimethylformamide (350 ml) and subjected to reaction overnight under reflux; thereafter, N,N-dlmethylformamide was distilled off under vacuum. Water (250 ml) was added to the residue and the mixture was stirred well, with the floating solids being subsequently recovered by filtration. The solids were dried, then recrystallized from methanol/methylene chloride, thereby yielding (1,4-benzodioxan-2-ylmethyl)phthalimide as a colorless tabular crystal in an amount of 8.43 g. The thus obtained crystal was dissolved in ethanol (500 ml); to the solution, hydrazine hydrate (4.3 g) was added, followed by refluxing under heating for 3 h. The resulting solids were filtered off and ethanol was distilled off under vacuum, followed by addition of water (300 ml). Thereafter, an aqueous solution of 6N sodium hydroxide was added to adjust pH to 12 and the mixture was subjected to 3 cycles of extraction with methylene chloride. The methylene chloride layers were dried with anhydrous sodium sulfate, and concentrated under vacuum, thereby yielding a crude product of 2-aminomethyl-1,4-benzodioxane as a colorless oil (crude product, 4.3 g).

후처리

  1. customsubjected to reaction overnight
  2. temperatureunder reflux
  3. distillationthereafter, N,N-dlmethylformamide was distilled off under vacuum
  4. additionWater (250 ml) was added to the residue
  5. filtrationbeing subsequently recovered by filtration
  6. customThe solids were dried
  7. customrecrystallized from methanol/methylene chloride
  8. dissolutionThe thus obtained crystal was dissolved in ethanol (500 ml)
  9. additionto the solution, hydrazine hydrate (4.3 g) was added
  10. temperatureby refluxing
  11. temperatureunder heating for 3 h
  12. filtrationThe resulting solids were filtered off
  13. distillationethanol was distilled off under vacuum
  14. additionfollowed by addition of water (300 ml)
  15. additionThereafter, an aqueous solution of 6N sodium hydroxide was added
  16. extractionthe mixture was subjected to 3 cycles of extraction with methylene chloride
  17. dry with materialThe methylene chloride layers were dried with anhydrous sodium sulfate
  18. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-4e049f7f95094f20b49b427909f24510
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480905

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