Benzyl Bromide → N-Boc-N-benzyl-3-chloropropylamine

HRID 321948ノート

反応式

HRID 321948 の反応式
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][Cl:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.CCOCC.O>[C:1]([N:8]([CH2:9][CH2:10][CH2:11][Cl:12])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10932310N-Boc-3-Chloropropylamine

生成物 1

HCID 11098062N-Boc-N-benzyl-3-chloropropylamine収率 13.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-Boc-3-chloropropylamine (10.0 g, 51.8 mmol) in THF was added sodium hydride (1.87 g, 78 mmol). After 20 min, benzyl bromide (9.24 mL, 78 mmol) was added and the reaction mixture was heated at reflux for 16 h. After cooling, the reaction mixture was diluted with Et2O (150 mL) and H2O (50 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give N-Boc-N-benzyl-3-chloropropylamine (1.97 g, 13% yield) as a pale yellow oil.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted twice with Et2O
  6. washThe combined organic phases were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-256e366c627e4932a36fa4f2e340f0d0
出典データセット
uspto-grants-2001_04
特許番号
US06211170B1

反応ノート

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