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

HRID 1442640Notes

Reaction equation

HRID 1442640 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>CCOC(C)=O.[Pd]>[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 1

HCID 7835221-(4-Nitrobenzyl)pyrrolidine

Product 1

HCID 7768524-(Pyrrolidin-1-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd/C (500 mg) was added to a solution of 1-(4-nitrobenzyl)-pyrrolidine Compound 1n3 (4.56 g, 22.1 mmol) in EtOAc (20 mL). The mixture was hydrogenated at 50 PSI for a period of 2 hrs and filtered through Celite. The filtrate was evaporated and the residue was dissolved in 10% NH4Cl and washed with ethyl ether. The aqueous layer was then adjusted to pH 10 with NaOH and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to give 4-pyrrolidin-1-ylmethyl-phenylamine Compound 1n (3.05 g) as a light brown oil. 1H NMR (CDCl3) δ 7.10 (d, J=8.5 Hz, 2H); 6.63 (d, J=8.5 Hz, 2H); 3.60 (br s, 2H); 3.50 (s, 2H); 2.52-2.42 (m, 4H); 1.83-1.69 (m, 4H).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in 10% NH4Cl
  4. washwashed with ethyl ether
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-d1af0873870f42eb88b1d35670a3d099
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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