Nitrate → 5-(4-Aminobenzyl)-1-methylpyrrolidin-2-one

HRID 1278084Notes

Reaction equation

HRID 1278084 reaction equation
C(C1[NH:12]C(=O)CC1)C1C=CC=CC=1.CI.C(=O)([O-])[O-].[K+].[K+].[N+]([O-])([O-])=O.[CH2:26]([CH:33]1[N:37]([CH3:38])[C:36](=[O:39])[CH2:35][CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N+]([O-])(O)=O.S(=O)(=O)(O)O>CC(CC)=O>[NH2:12][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH:33]2[N:37]([CH3:38])[C:36](=[O:39])[CH2:35][CH2:34]2)=[CH:28][CH:29]=1

Participants

8

Reactant 6

HCID 943NitrateHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 998815-Benzylpyrrolidin-2-OneHCID 200623795-Benzyl-1-methylpyrrolidin-2-oneHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 234525985-(4-Aminobenzyl)-1-methylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methylate 5-benzylpyrrolidin-2-one with methyl iodide in the presence of potassium carbonate in ethyl methyl ketone; nitrate the thus-obtained 5-benzyl-1-methylpyrrolidin-2-one with nitric acid/sulfuric acid, pour the resulting reaction product onto ice water, extract it with methylene chloride, evaporate solvent from the extract and hydrogenate the thus-obtained 1-methyl-5-(4-nitrobenzyl)pyrrolidin-2-one with platinum/hydrogen without further purification to obtain 5-(4-aminobenzyl)-1-methylpyrrolidin-2-one.

Workup

  1. customthe resulting reaction product onto ice water
  2. extractionextract it with methylene chloride
  3. customevaporate solvent from the
  4. extractionextract
  5. customwithout further purification

Sources & evidence

ORD record
ord-56a611f10c1349b581a1012291d37a03
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…