Water → (4-Chlorophenyl)(cyclopropyl)methanamine

HRID 423024ノート

反応式

HRID 423024 の反応式
O1CCCC1.B.CO[N:9]=[C:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:11]1[CH2:13][CH2:12]1.O.[OH-].[Na+]>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]([CH:11]2[CH2:12][CH2:13]2)[NH2:9])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 73696106(4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime2 回

生成物 1

HCID 5155531(4-Chlorophenyl)(cyclopropyl)methanamine収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Borane tetrahydrofuran complex (1N in THF, 65.6 mL) was added to (4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime (Intermediate 2) (2.75 g) in THF (100 mL) at 25° C. under nitrogen. The resulting solution was stirred at reflux for 3 hours, then cooled to 0° C. Water was carefully added, followed by aqueous NaOH (20%, 100 mL). The resulting mixture was stirred at reflux overnight, then allowed to cool to room temperature. The product was extracted into hexane, then dried over sodium sulfate, filtered and evaporated to afford (4-chlorophenyl)(cyclopropyl)methanamine as a clear oil (2.205 g, 93%).

後処理

  1. temperatureat reflux for 3 hours
  2. stirringThe resulting mixture was stirred
  3. temperatureat reflux overnight
  4. temperatureto cool to room temperature
  5. extractionThe product was extracted into hexane
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-56fa5e93847f44a6a4ec4bcb8ece001f
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

反応ノート

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