Aluminium lithium hydride → (4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)methanamine

HRID 1264078

反応式

HRID 1264078 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:12][CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=O)=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][NH2:21])=[CH:22][CH:23]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 221374564-[2-(1-Pyrrolidinyl)ethoxy]benzamide

生成物 1

HCID 14425929(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)methanamine収率 101.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (132 mg, 3.49 mmol, 2.1 eq.) was added to a solution of 4-[2-(1-pyrrolidinyl)ethoxy]benzamide (389 mg, 1.66 mmol) in dry THF (25 mL) then the reaction heated at reflux for 20 h. The reaction was allowed to cool to ambient temperature then quenched with water (0.250 mL). Aqueous sodium hydroxide (0.250 mL of 15% w/v) then water (0.750 mL) was added and the reaction stirred for 30 min. The reaction mixture was passed through a pad of diatomaceous earth which was washed with THF (3×15 mL). The combined organics were concentrated under reduced pressure to give the amine as oil (372 mg, >100%) which was used without further purification.

後処理

  1. temperaturethe reaction heated
  2. temperatureat reflux for 20 h
  3. customthen quenched with water (0.250 mL)
  4. additionAqueous sodium hydroxide (0.250 mL of 15% w/v) then water (0.750 mL) was added
  5. washwas washed with THF (3×15 mL)
  6. concentrationThe combined organics were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b86e565b11d34e2b9e72f2191fa827f4
出典データセット
uspto-grants-2003_04
特許番号
US06541499B1

関連ノート

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