All Notebooks | Help | Support | About
7th May 2013 @ 02:26
Mnr: MNR101-110

Synthesis of 1-(4-fluorobenzyl)piperazine as a coupling partner to make TCMDC-132385

Following procedure from DOI: 10.1021/jm900722z - General Procedure for 1-Benzylpiperazines 35-36  

 

As for Synthesis of 1-(4-fluorobenzyl)piperazine - MNR107-1

Hazard Assessment

 

HIRAC MNR107.pdf

Procedure

Anhydrous piperazine (4.32 g 50.2 mmol) was added to THF (17 mL) and the mixture was heated to reflux until the piperazine was fully dissolved. To the solution was added 4-fluorobenzyl chloride (1.0 mL, 8.37 mmol) dropwise.  A white precipitate was formed immediately.  The reaction mixture was refluxed for 1 hour and then allowed to cool to room temperature.  The excess piperazine was filtered off and washed with EtOAc (30 mL). The organic layer was concentrated.  The crude white sollid was washed with KOH solution (pH >12) (40 mL) and the the aqueous layer was extracted with DCM (3 x 50mL).  The organic layers were combined, dried, filtered concentrated to give a cloudy white oil (1.759 g, >8.37 mmol, >100%) 

NMR

mnr107-2_crude_1H.pdf
mnr107-2_crude.zip
- contains traces of DCM and EtOAc

Conclusion

Reaction proceeded as before and crude 1H NMR was consistent as before.  Crude product was dried further under hi-vac before being taken on to the next step without further purification.  


Strings


Starting Material

InChI=1S/C7H6ClF/c8-5-6-1-3-7(9)4-2-6/h1-4H,5H2

InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2

Product

InChI=1S/C11H15FN2/c12-11-3-1-10(2-4-11)9-14-7-5-13-6-8-14/h1-4,13H,5-9H2

Attached Files
mnr107-2_crude_1H.pdf
mnr107-2_crude.zip