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

HRID 2271075

反応式

HRID 2271075 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-93b93d08e3624776bc1faf292198668e
出典データセット
uspto-grants-2001_12
特許番号
US06333349B1

関連ノート

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