3,4-Dichlorobenzyl chloride → HCID 43130924, compound

HRID 2110030Notes

Reaction equation

HRID 2110030 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:19]Cl>C(#N)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH2:19][N:6]2[CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4][CH2:5]2)[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 235274-(Aminomethyl)piperidine

Product 1

HCID 43130924HCID 43130924, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving 4-aminomethylpiperidine (13.7 g, 120 mmol) in acetonitrile (200 ml), potassium carbonate (11.057 g, 80 mmol) and 3,4-dichlorobenzyl chloride (7.818 g, 40 mmol) were added and the mixture was stirred at 60° C. overnight. After completion of the reaction, the reaction mixture was filtered and the solvent was distilled off. Purification was performed by silica gel column chromatography (dichloromethane/methanol/triethylamine=90/5/5) to obtain {1-[(3,4-dichlorophenyl)methyl]-4-piperidyl}methylamine. The compound was identified by LC-MS.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. distillationthe solvent was distilled off
  5. customPurification

Sources & evidence

ORD record
ord-d5759ce30e5b4e10b0204c6452f08556
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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