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

HRID 868138Notes

Reaction equation

HRID 868138 reaction equation
[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.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[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

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 14280891N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2.91 g (11.8 mmol) N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide and 15 ml anhydrous tetrahydrofuran was dropped into a suspension of 1.41 g (35 mmol) lithium aluminum hydride and 30 ml tetrahydrofuran. The reaction was refluxed overnight then cooled to room temperature. To the solution was added 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 dichlromethane, 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.

Workup

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

Sources & evidence

ORD record
ord-6a6fdd4978f347cfa69b5d30c01bdb8f
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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