Hydrochloric Acid → (3R)-1-benzylpyrrolidin-3-amine

HRID 232050

Reaction equation

HRID 232050 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN.Cl>CO>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14555490[R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1519354(3R)-1-benzylpyrrolidin-3-amineYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 30.6 g (0.1 mol) of [R]-2-[1-(phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione in 300 ml of methanol was treated with 6.4 g (0.2 mol) of hydrazine. The reaction was stirred at room temperature for 18 hours and treated with 12.5 ml (0.15 mol) of concentrated hydrochloric acid. The solid was removed by filtration; the precipitate was washed with ethanol and the filtrate evaporated in vacuo. The residue was dissolved in water, made basic with 20% sodium hydroxide saturated with sodium chloride and extracted with ether (3×250 ml). The combined ether layers were washed with saturated sodium chloride solution, dried (MgSO4), filtered and evaporated in vacuo. The residue was distilled in high vacuo to give 14.4 g of the title compound, bp 86°-87°/0.15 mm.

Workup

  1. customThe solid was removed by filtration
  2. washthe precipitate was washed with ethanol
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether (3×250 ml)
  6. washThe combined ether layers were washed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. distillationThe residue was distilled in high vacuo

Sources & evidence

ORD record
ord-61554d553e0145c7ba34cda62cf1017e
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Linked notes

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