1-(4-Nitrobenzyl)pyrrolidine → 4-(Pyrrolidin-1-ylmethyl)aniline

HRID 1785294Notes

Reaction equation

HRID 1785294 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.ClCCl.CO>C(O)C>[N:9]1([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:15][CH:14]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7835221-(4-Nitrobenzyl)pyrrolidineHCID 21226129Dichloromethane methanol

Product 1

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-nitro-benzyl)-pyrrolidine (1.37 g) in ethanol (66 mL) tin(II)-chloride dihydrate (9.0 g) was added portionwise and the resulting mixture refluxed for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the aqueous phase extracted with additional ethyl acetate, the combined organic phases dried (Na2SO4) and evaporated, which gave, after chromatography on silica using dichloromethane/methanol, the title compound (432 mg).

Workup

  1. temperaturethe resulting mixture refluxed for 2 h
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. extractionthe aqueous phase extracted with additional ethyl acetate
  4. dry with materialthe combined organic phases dried (Na2SO4)
  5. customevaporated
  6. customwhich gave

Sources & evidence

ORD record
ord-c3995c5ded094789b555339d723dd692
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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