Nitric Acid → 2-(4-Nitrobenzyl)-1-methylpyrrolidine

HRID 1278050Notes

Reaction equation

HRID 1278050 reaction equation
[CH2:1]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>S(=O)(=O)(O)O>[N+:14]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:3][CH:4]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 10261602benzyl methylpyrrolidine

Product 1

HCID 131869052-(4-Nitrobenzyl)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Dissolve 27.9 g of 2-benzyl-1-methylpyrrolidine in 130 ml of conc. sulfuric acid, and add 100 ml of conc. nitric acid dropwise at 0°, with stirring, to the resulting solution. Continue stirring for a further 30 minutes at room temperature. Pour the mixture into 1 liter of ice water and alkalize with sodium hydroxide solution, with cooling. Extract the thus-produced preparation 4 times with, in each case, 150 ml of diethyl ether. Dry the ether phase over sodium sulfate and concentrate it to a red oil to obtain the title compound at a yield of 33.8 g (96% of theory). The hydrogen fumarate (from isopropanol) melts at 145° to 146°.

Workup

  1. stirringContinue stirring for a further 30 minutes at room temperature
  2. temperaturewith cooling
  3. extractionExtract
  4. customthe thus-produced preparation 4 times with, in each case, 150 ml of diethyl ether
  5. dry with materialDry the ether phase over sodium sulfate
  6. concentrationconcentrate it to a red oil

Sources & evidence

ORD record
ord-e471c32fd60d458ba4e60c942b634711
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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