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16th April 2012 @ 04:30
START: 16/04/12


Hazard and Risk Assessment
As for KAB21-2 (here).

Previous Experiments
TFA mediated synthesis of 6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline (KAB24-3)
Synthesis of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB21-2)
TFA mediated synthesis of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB21-3)

Following Experiments

Chemical Information
N-[2-(3,4-Dimethoxyphenyl)ethyl]-1-phenylmethanimine (1, KAB19-2) SMILES: O(c1ccc(cc1OC)CC/N=C/c2ccccc2)C, InChI: InChI=1S/C17H19NO2/c1-19-16-9-8-14(12-17(16)20-2)10-11-18-13-15-6-4-3-5-7-15/h3-9,12-13H,10-11H2,1-2H3/b18-13+, InChIKey: HEYKSOUNCDDROU-QGOAFFKASA-N
6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (2, KAB21-4) - SMILES: O(c1c(OC)cc3c(c1)C(c2ccccc2)NCC3)C, InChI: InChI=1S/C17H19NO2/c1-19-15-10-13-8-9-18-17(12-6-4-3-5-7-12)14(13)11-16(15)20-2/h3-7,10-11,17-18H,8-9H2,1-2H3, InChIKey: GZGZWZVAJDFXJK-UHFFFAOYSA-N

16/04/12. KAB19-2 (365 mg, 1.36 mmol, 1 equiv.) was dissolved in toluene (35 mL) before the addition of trifluoroacetic acid (0.05 mL, 0.7 mmol, 0.5 equiv.). The reaction mixture was reflux heated to 110 °C from 14:50.
Reaction mixture before the addition of TFA
Reaction mixture after the addition of TFA

Monitoring the Reaction Progress by TLC
TLC of reaction mixture (5 min)

All TLCs were eluted with 15%, methanol/dichloromethane, v/v and stained with ninhydrin.

Crude yield (208 mg, 57%)

Summary and Conclusion

NOTES 16/04/12
- KAB19-2 had crystallised since the last time it was used (in KAB21-3). Previously it was an oil.

Flask: 50.4746 g
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Attached Files
Scheme KAB21-4
Reaction mixture before the addition of TFA
Reaction mixture after the addition of TFA
TLC of reaction mixture (5 min)