Water → N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine

HRID 1198604ノート

反応式

HRID 1198604 の反応式
[CH3:1][N:2]([CH3:18])[C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]([CH3:18])[CH2:3][CH:5]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 14280891N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 14280892N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine収率 58.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2.91 g (11.8 mmol) N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide and 15 mL anhydrous tetrahydrofuran was added dropwise into a suspension of 1.41 g (35 mmol) lithium aluminum hydride in 30 mL tetrahydrofuran. The reaction was refluxed overnight then cooled to room temperature. To the solution was added dropwise successively 1.5 mL water, 1.5 mL 15% sodium hydroxide and 4.5 mL of water. The resulting precipitate was filtered. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue was bulb to bulb distilled giving 1.5 g (58%) of N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as a clear liquid. This material was used in the next step.

後処理

  1. temperatureThe reaction was refluxed overnight
  2. filtrationThe resulting precipitate was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated under reduced pressure
  7. distillationdistilled

出典と根拠

ORDレコード
ord-65ef5fb1ccb04479858f3327fc504351
出典データセット
uspto-grants-1994_01
特許番号
US05281612

反応ノート

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