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14th March 2012 @ 09:06
START: 13/03/12

Scheme KAB20-1

Hazard and Risk Assessment

Previous Experiments
Synthesis of N-benzylidene-N-phenethylamine (KAB18-1)

Following Experiments

Chemical Information
N-Benzylidene-N-phenethylamine (1, KAB18-1) - SMILES: N(=C/c1ccccc1)\CCc2ccccc2, InChI: InChI=1S/C15H15N/c1-3-7-14(8-4-1)11-12-16-13-15-9-5-2-6-10-15/h1-10,13H,11-12H2/b16-13+, InChIKey: OOBAKFDIGIHHOM-DTQAZKPQSA-N
Silver triflate - SMILES: C(F)(F)(F)S(=O)(=O)[O-].[Ag+], InChI: InChI=1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1, InChIKey: QRUBYZBWAOOHSV-UHFFFAOYSA-M
1-Phenyl-1,2,3,4-tetrahydroisoquinoline (2, KAB20-1) - SMILES: c1ccc3c(c1)C(c2ccccc2)NCC3, InChI: InChI=1S/C15H15N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9,15-16H,10-11H2, InChIKey: PRTRSEDVLBBFJZ-UHFFFAOYSA-N

Starting material solution: KAB18-1 (145.2 mg) was dissolved in dried and degassed toluene (1 mL) before the addition of activated molecular sieves (4A).
The toluene used was degassed using the freeze-thaw method (liquid nitrogen) and dried with molecular sieves (4A). All glassware was oven dried prior to use.

13/03/12. 207 μL of the prepared KAB18-1/toluene solution (30 mg, 140 mmol, 1 eq) was added to stirring toluene (2.8 mL) before the addition of silver triflate (22.7 mg, 0.880 mmol, 0.62 eq). The reaction mixture was left to stir in the dark, under a nitrogen atmosphere at rt from 17:30.
14/03/12. After 24 hours, the reaction mixture was diluted with EtOAc (30 mL) then washed with saturated sodium bicarbonate solution (30 mL). The basic aqueous layer was extracted with EtOAc (3 × 20 mL). The organic layers were combined, dried over magnesium sulfate, filtered then concentrated under reduced pressure to give crude KAB20-1.

Summary and Conclusion

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Scheme KAB20-1