1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

HRID 845114ノート

反応式

HRID 845114 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2([C:16]#[N:17])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[C:7]1([C:13]2([CH2:16][NH2:17])[CH2:14][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 702871-Phenylcyclopropanemethanamine収率 74%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

LiAlH4 (1.8 g, 48 mmol) is added in batches over 5 min to a solution of 1-phenylcyclopropane carbonitrile (6.58 g, 46 mmol) in ether (200 mL) stirred under N2 at 0°. After 1 h the reaction mixture is quenched by a careful dropwise addition of water (1.8 mL), 10% W/V NaOH solution (1.8 mL) and water (5.4 mL). Vigorous gas evolution again occurs. The mixture is vacuum filtered, and the filtrate is extracted with dilute HCl (0.2M, 3×100 mL). The combined extracts are washed with ether (3×100 mL) and made basic with NaOH pellets (3.2 g, 80 mmol). The aqueous layer is extracted with ether (3×100 mL). The combined organic phases are washed with water (2×100 mL), saturated brine (100 mL) and dried (MgSO4). The solvent is removed under reduced pressure to give (1-phenylcyclopropyl)methylamine (4.98 g, 74%) as an orange oil. Nmr δ (CDCl3) 7.1-7.5 (5H, m), 2.77 (2H, S), 1.3 (2H, br s), 0.6-0.95 (4H, m).

後処理

  1. customAfter 1 h the reaction mixture is quenched by a careful dropwise addition of water (1.8 mL), 10% W/V NaOH solution (1.8 mL) and water (5.4 mL)
  2. filtrationfiltered
  3. extractionthe filtrate is extracted with dilute HCl (0.2M, 3×100 mL)
  4. washThe combined extracts are washed with ether (3×100 mL)
  5. extractionThe aqueous layer is extracted with ether (3×100 mL)
  6. washThe combined organic phases are washed with water (2×100 mL), saturated brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-3d1ad73a151845d7a6bb64ca99864519
出典データセット
uspto-grants-1988_07
特許番号
US04755594

反応ノート

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