4-Nitrobenzyl chloride → 1-(4-Nitrobenzyl)pyrrolidine

HRID 1442639Notes

Reaction equation

HRID 1442639 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1.[NH4+].[Cl-]>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 7835221-(4-Nitrobenzyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

4-nitrobenzyl chloride Compound 1n1 (4.0 g, 23.3 mmol) and pyrrolidine Compound 1n2 (4.8 mL, 58.3 mmol) were combined in THF (50 mL) at ambient temperature. After 18 hr, the reaction was diluted with 10% NH4Cl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to provide 1-(4-nitrobenzyl)-pyrrolidine Compound 1n3 (4.7 g) as a pale yellow oil without further purification (prepared as described in Mitsuru Shiraishi, et al., J. Med. Chem., 2000, 43, 2049-2063). 1H NMR (CDCl3) δ 8.17 (d, J=8.6 Hz, 2H); 7.51 (d, J=8.6 Hz, 2H); 3.72 (s, 2H); 2.58-2.48 (m, 4H); 1.89-1.72 (m, 4H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec37bccafa1447808447e93a9152b5b8
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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