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

HRID 2236576Notes

Reaction equation

HRID 2236576 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[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CCN(CC)CC>C1COCC1>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 8082PiperidineHCID 8471Triethylamine

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-Nitrobenzyl chloride (0.086 g, 0.501 mmol) is dissolved in THF (1 mL), and to this solution, is added piperidine (0.059 mL, 0.601 mmol) followed by Et3N (0.210, 1.50 mmol). After stirring the mixture at 50° C. for 5 h, the resulting solution is filtered, and then the solvent is removed via high vacuum to afford the product (0.090 g, 82%); 1H NMR (DMSO-d6) δ 1.25-1.35 (m, 2H), 1.40-1.48 (m, 4H), 2.23-2.32 (m, 4H), 3.47 (s, 2H), 7.50 (d, J=8.8 Hz, 2H), 8.11 (d, J=8.8 Hz, 2H); mass spectrum [(+) ESI], m/z 221 (M+H)+.

Workup

  1. filtrationthe resulting solution is filtered
  2. customthe solvent is removed via high vacuum

Sources & evidence

ORD record
ord-45c452c44a0e4b038252c746ab69e623
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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