Sodium Azide → 1-Phenyl-cyclopropylamine

HRID 14056

反応式

HRID 14056 の反応式
[N-:1]=[N+]=[N-].[Na+].[C:5]1([C:11]2(C(O)=O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>S(=O)(=O)(O)O.ClCCl>[C:5]1([C:11]2([NH2:1])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 802061-Phenylcyclopropanecarboxylic acid

生成物 1

HCID 1945491-Phenyl-cyclopropylamine

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

Following the procedure described in N. W. Werner et. al., J. Org. Syn. Coll. Vol. 5, 273-276, sodium azide (0.915 g, 14.1 mmol) is slowly added to a solution of 1-phenyl-cyclopropanecarboxlic acid (1.0 g, 6.1 mmol) in concentrated sulfuric acid (5 ml) and dichloromethane (10 ml). The sodium sulfate precipitated out of solution. The reaction mixture is heated to 50 degrees C. for 17 hours and then cooled to 0 degrees C. The mixture is basified to pH=11 with sodium hydroxide (1N) and extracted with dichloromethane (2×). The organic layers are combined, dried over sodium sulfate, filtered and concentrated. The residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1) to give the title compound, MS (ESI+) for C9H11N m/z (M+H)+=134.

後処理

  1. customThe sodium sulfate precipitated out of solution
  2. temperaturecooled to 0 degrees C
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1)

出典と根拠

ORDレコード
ord-b6b12c4b583a4f42ba7d7ac0bdcfa0de
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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