Ammonia → 2,3,4,5-Tetrahydro-1-benzoxepin-5-amine

HRID 2271075

반응식

HRID 2271075 반응식
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[N:12]O)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O.N>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[NH2:12][CH:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3][CH2:4]1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 962WaterHCID 4311764Sodium borohydrideHCID 732003533,4-dihydro-1-benzoxepin-5(2H)-one oxime

생성물 1

HCID 156196982,3,4,5-Tetrahydro-1-benzoxepin-5-amine수율 113.9%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

A solution of 2.0 g (11.3 mmol) of 3,4-dihydro-1-benzoxepin-5(2H)-one oxime in 15 ml of 1,2-dimethoxyethane (DME) was added dropwise at 0° C. under argon to a mixture of 4.5 g (23.7 mmol) of titanium tetrachloride and 1.79 g (47.4 mmol) of sodium borohydride in 50 ml of DME over the course of 20 min. After stirring at RT for 2 days, 100 ml of water were added dropwise and the mixture was rendered alkaline using conc. ammonia solution. After filtering off the precipitate with suction, the filtrate was extracted three times with EA. After washing with sodium chloride solution, drying over magnesium sulfate and concentrating, 2.1 g of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine were obtained.

후처리

  1. filtrationAfter filtering off the precipitate with suction
  2. extractionthe filtrate was extracted three times with EA
  3. washAfter washing with sodium chloride solution
  4. dry with materialdrying over magnesium sulfate
  5. concentrationconcentrating

출처 및 근거

ORD 기록
ord-93b93d08e3624776bc1faf292198668e
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333349B1

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