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

HRID 1198604Notes

Reaction equation

HRID 1198604 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.[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

Participants

6

Reactant 4

HCID 962Water2×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 8028TetrahydrofuranSolvent2×

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 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.

Workup

  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

Sources & evidence

ORD record
ord-65ef5fb1ccb04479858f3327fc504351
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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