1-Chloro-4-(chloromethyl)benzene → {[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amine
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:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CC#N>[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH2:5][CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 4-(aminomethyl)piperidine (7.00 g, 61.3 mmol) in CH3CN (100 mL) was treated sequentially with K2CO3 (3.02 g) and 4-chlorobenzyl chloride (3.52 g, 21.8 mmol). The reaction mixture was heated to 60° C. for 16 h, cooled to 25° C. and concentrated. The residue was partitioned between CH2Cl2 (75 mL) and water (50 mL), and was washed with water (2×50 mL) and brine (1×50 mL). The organic phase was dried (MgSO4) and concentrated. Chromatography (SiO2, 4% H2O-iPrOH) afforded4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (3.58 g, 69%).
Workup
- temperaturecooled to 25° C.
- concentrationconcentrated
- customThe residue was partitioned between CH2Cl2 (75 mL) and water (50 mL)
- washwas washed with water (2×50 mL) and brine (1×50 mL)
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5d4248cec91a4c448519730ebdb6bc0a
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362177B1
Reaction notes
Loading…