Piperazine → 1-(3-Phenylpropyl)piperazine
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:5]1([CH2:4][CH2:3][CH2:2][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of 1-chloro-3-phenylpropane (5.4 g) in toluene (10 ml) was added to a stirred solution of piperazine (15.0 g) and triethylamine (3.5 g) in toluene (20 ml) at 100° C. The reaction mixture was heated with stirring at 100° C. for 0.2 hours and then heated under reflux for 18 hours. The reaction mixture was allowed to cool to room temperature and then filtered. The filtrate was evaporated and the residual oil was purified by column chromatography, eluting with dichloromethane/methanol (19:1), then methanol, to give 1-(3-phenylpropyl)piperazine as an oil.
Workup
- temperatureThe reaction mixture was heated
- temperatureheated
- temperatureunder reflux for 18 hours
- temperatureto cool to room temperature
- filtrationfiltered
- customThe filtrate was evaporated
- customthe residual oil was purified by column chromatography
- washeluting with dichloromethane/methanol (19:1)
Sources & evidence
- ORD record
- ord-8bc49faf62e14f45913c79ee48b4ba40
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05741800
Reaction notes
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