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

HRID 2105294Notes

Reaction equation

HRID 2105294 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1.[NH4+].[Cl-]>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 8082Piperidine

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

1-chloromethyl-4-nitro-benzene Compound 1i (5.0 g, 29 mmol) and piperidine (5.8 mL, 58 mmol) were combined in THF (30 mL) at ambient temperature. The reaction was refluxed for 4 hours, then diluted with aqueous 10% NH4Cl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to provide 1-(4-nitro-benzyl)-piperidine Compound 1j (5.0 g) as a pale yellow oil requiring no further purification (see, Mitsuru Shiraishi, et al., J. Med. Chem., 2000, 43, 2049-2063). 1H NMR (DMSO-d6) δ 8.18 (d, 2H); 7.59 (d, 2H); 3.57 (s, 2H); 2.43-2.25 (m, 4H); 1.58-1.32 (m, 6H).

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-92c91130e1b24ea8a75d9f1d494b7776
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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