1-Chloro-4-(chloromethyl)benzene → {[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amine

HRID 133586

Reaction equation

HRID 133586 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Cl)=[CH:10][CH:9]=1.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(#N)C>[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:12][C:11]2[CH:14]=[CH:15][C:8]([Cl:7])=[CH:9][CH:10]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 235274-(Aminomethyl)piperidine

Product 1

HCID 18426145{[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amineYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

K2CO3 (3.02 g) and 4-chlorobenzyl chloride (3.52 g, 21.8 mmol) were successively added to an acetonitrile (100 mL) solution of 4-(aminomethyl)piperidine (7.00 g, 61.3 mmol). The resulting reaction mixture was stirred at 60° C. for 16 hours, cooled to 25° C. and concentrated. The obtained residue was fractionated between dichloromethane (75 mL) and water (50 mL) and then washed with water (50 mL×2) and brine (50 mL×1). The organic layer was dried (over MgSO4), concentrated and then purified by chromatography (SiO2, 4% H2O-iPrOH) to provide 4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (3.58 g, 69%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to 25° C.
  3. concentrationconcentrated
  4. washwashed with water (50 mL×2) and brine (50 mL×1)
  5. dry with materialThe organic layer was dried (over MgSO4)
  6. concentrationconcentrated
  7. custompurified by chromatography (SiO2, 4% H2O-iPrOH)

Sources & evidence

ORD record
ord-f1d42b141bc340a0a10ca3237623865e
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Linked notes

Loading…