Sodium Hydroxide → 1-Benzyl-4-methylpyrrolidin-3-amine

HRID 358909Notes

Reaction equation

HRID 358909 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[CH2:14][CH:13]([CH3:15])[C:12](=[N:16]O)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.[Ni]>[CH2:3]([N:10]1[CH2:14][CH:13]([CH3:15])[CH:12]([NH2:16])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 859932571-Benzyl-3-(hydroxyimino)-4-methylpyrrolidine

Product 1

HCID 142112411-Benzyl-4-methylpyrrolidin-3-amineYield 712.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

90 ml of a 20% w/v aqueous solution of sodium hydroxide were added to a solution of 12 g (0.059 mole) of 1-benzyl-3-(hydroxyimino)-4-methylpyrrolidine [prepared as described in Step (5) above] dissolved in 100 ml of ethanol. 23.9 g of Raney nickel (about 50%) were gradually added to the mixture, whilst vigorously stirring it. After the reaction mixture had been stirred for 3 hours, it was filtered. The upper layer of the filtrate was separated and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with methanol, to give 80 g of 1-benzyl-3-amino-4-methylpyrrolidine as a pale yellow liquid.

Workup

  1. stirringAfter the reaction mixture had been stirred for 3 hours
  2. filtrationit was filtered
  3. customThe upper layer of the filtrate was separated
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel
  6. washeluted with methanol

Sources & evidence

ORD record
ord-dfc7eee44f354ab08a1dd587cccbb18a
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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