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12th March 2012 @ 08:50
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Summary and Conclusion
The imine (KAB19-1) was facilely formed at room temperature upon addition of 3,4-dimethoxyphenethylamine to a concentrated mixture of benzaldehyde in diethyl ether.
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START: 13/03/12
FINISH: 15/03/12

Scheme KAB19-1



Hazard and Risk Assessment
Hazard and Risk Assessment KAB19-1


Following Experiments
Synthesis of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB21-1)

Chemical Information
3,4-Dimethoxyphenethylamine (1) - SMILES: O(c1ccc(cc1OC)CCN)C, InChI: InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3, InChIKey: ANOUKFYBOAKOIR-UHFFFAOYSA-N.
H-NMR (MeO)2PEA
H-NMR (MeO)2PEA

Benzaldehyde (2)- SMILES: c1ccc(cc1)C=O, InChI: InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H, InChIKey: HUMNYLRZRPPJDN-UHFFFAOYSA-N.
N-[2-(3,4-Dimethoxyphenyl)ethyl]-1-phenylmethanimine (3, KAB19-1) 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

Procedure
3,4-Dimethoxyphenethylamine (2 mL, 12 mmol, 1 eq) was added to stirring diethyl ether (4 mL) before benzaldehyde (1.2 mL, 12 mmol, 1 eq) was added slowly. The pale yellow solution turned a darker yellow and an miscible aqueous layer was visible in the bottom of the flask. After 20 minutes, the reaction mixture was dried over magnesium sulfate, filtered, then concentrated under reduced pressure to give a yellow oil.
H-NMR crude KAB19-1
Raw H-NMR crude KAB19-1

Proton NMR of the isolated product showed trace amounts of solvent and the benzaldehyde and 3,4-dimethoxyphenethylamine starting materials.

Summary and Conclusion
The imine (KAB19-1) was facilely formed at room temperature upon addition of 3,4-dimethoxyphenethylamine to a concentrated mixture of benzaldehyde in diethyl ether.

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NOTES 13/03/12
- Will need to repeat to acquire accurate yield for the procedure.
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Linked Posts
Attached Files
Scheme KAB19-1
Hazard and Risk Assessment KAB19-1
H-NMR crude KAB19-1
Raw H-NMR crude KAB19-1
H-NMR (MeO)2PEA
H-NMR (MeO)2PEA