Benzylamine → HCID 19047594, compound

HRID 1780771Notes

Reaction equation

HRID 1780771 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=O)[CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH:11]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 274831Ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate

Product 1

HCID 19047594HCID 19047594, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.7 g of 1-benzyl-3-carboethoxy-4-pyrrolidone and 10.7 g of benzylamine were added to 100 ml of benzene, and then dehydrated with Dean-Stark distillation apparatus. The residual benzene was evaporated. The residue was dissolved in 200 ml of tetrahydrofuran, and then a small amount of methyl orange was added. To this was added methanol saturated with hydrogen chloride to adjust the pH to about 4, and then 7 g of sodium cyanoborohydride was added thereto. A solution of methanol saturated with hydrogen chloride was added dropwise to the reaction solution with stirring until the pink-color of the solution did not disappear. The reaction solution was basified with 15% aqueous caustic soda solution, and then the reaction mixture was diluted with ether, after which the aqueous layer was separated the aqueous layer was removed by addition of ether. The organic layer was dried over anhydrous magnesium sulfate, evaporated under reduced pressure, and then subjected to silica gel column chromatography (hexane:ethyl acetate, 5:1(v/v)) to obtain 24 g of the desired compound (yield: 71%).

Workup

  1. distillationdehydrated with Dean-Stark distillation apparatus
  2. customThe residual benzene was evaporated
  3. dissolutionThe residue was dissolved in 200 ml of tetrahydrofuran
  4. additiona small amount of methyl orange was added
  5. additionTo this was added methanol saturated with hydrogen chloride
  6. addition7 g of sodium cyanoborohydride was added
  7. additionA solution of methanol saturated with hydrogen chloride was added dropwise to the reaction solution
  8. additionthe reaction mixture was diluted with ether
  9. customafter which the aqueous layer was separated the aqueous layer
  10. customwas removed by addition of ether
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2d957fe77de8410f95f25968890c9172
Source dataset
uspto-grants-1997_05
Patent number
US05631266

Reaction notes

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