100g food grade glycine was placed in a 2L flask with 1L technical grade cyclohexanone and brought to steady reflux with strong magnetic stirring. The reaction mix darkened over the course of hours and it was thought the amount of glycine seen stirring in the flask was very slowly decreasing. The reflux was continued for 14 hours, at which point the reaction mixture was cooled, filtered and the filter cake weighed while still damp with cyclohexanone. Weight of filter cake 115g.
FAIL
From the journals it was hoped that cyclohexanone would have catalized the decarboxylation of glycine to methylamine and formed an imine with cyclohexanone, to be later hydrolized from the Schiff base N-cyclohexylidenemethanamine back to methylamine HCl.
These researchers imagine glycine just requires much more energetic reaction conditions then can be had at atmospheric pressure with this solvent and normal heating.
Proposed alternate experiments:
1) microwave reflux
2) pressure bomb
Is there a way N-cyclohexylidenemethanamine could be a solid at @150C?
Is there a way 2-(cyclohexylideneamino)acetic acid could have been produced? If so, we still aren't advancing. It and unreacted glycine would give glycine HCl with the addition of 3N HCl. This would however give hope to the proposed routes to (Z)-2-(1-phenylpropan-2-ylideneamino)acetic acid and time release/metabolized amphetamines or ethylamphetamines from strait reduction.
The cyclohexanone has yet to be hydrolyzed/extracted with 3N HCl and the aq. evaporated to check for methylamine. I will get around to it. After seeing all the starting glycine in the filter cake enthusiasm was lost.
Thermal decarboxylation of alpha-amino acids
Bulletin de la Societe Chimique de France (1965), (4), 929-33
"Amino acids (5 g.) suspended in 50 ml. of an inert solvent (C13to C18 paraffins, squalane, dodecene, dodecylbenzene, .alpha.-methyl-naphthalene, tetralin, decalin) were decarboxylated after 4-8 hrs. of reflux in the presence of 2% of a catalyst (tetralin or decalin peroxides, tetralone, cyclohexanone, acetophenone), to give the corresponding amines in 50-90% yield. Similarly, an amino acid suspension in a high boiling ketone (nonanone, cyclo-hexanone, acetophenone, 2-, 3-, and 4-methyleyclohexanone, p-methylacetophenone, benzyl methyl ketone, propiophenone, benzophenone) yielded by decarboxylation, a Schiff base which was hydrolyzed in 3N HCl to regenerate the ketone and to give the amine-HCl."
FAIL
From the journals it was hoped that cyclohexanone would have catalized the decarboxylation of glycine to methylamine and formed an imine with cyclohexanone, to be later hydrolized from the Schiff base N-cyclohexylidenemethanamine back to methylamine HCl.
These researchers imagine glycine just requires much more energetic reaction conditions then can be had at atmospheric pressure with this solvent and normal heating.
Proposed alternate experiments:
1) microwave reflux
2) pressure bomb
Is there a way N-cyclohexylidenemethanamine could be a solid at @150C?
Is there a way 2-(cyclohexylideneamino)acetic acid could have been produced? If so, we still aren't advancing. It and unreacted glycine would give glycine HCl with the addition of 3N HCl. This would however give hope to the proposed routes to (Z)-2-(1-phenylpropan-2-ylideneamino)acetic acid and time release/metabolized amphetamines or ethylamphetamines from strait reduction.
The cyclohexanone has yet to be hydrolyzed/extracted with 3N HCl and the aq. evaporated to check for methylamine. I will get around to it. After seeing all the starting glycine in the filter cake enthusiasm was lost.
Thermal decarboxylation of alpha-amino acids
Bulletin de la Societe Chimique de France (1965), (4), 929-33
"Amino acids (5 g.) suspended in 50 ml. of an inert solvent (C13to C18 paraffins, squalane, dodecene, dodecylbenzene, .alpha.-methyl-naphthalene, tetralin, decalin) were decarboxylated after 4-8 hrs. of reflux in the presence of 2% of a catalyst (tetralin or decalin peroxides, tetralone, cyclohexanone, acetophenone), to give the corresponding amines in 50-90% yield. Similarly, an amino acid suspension in a high boiling ketone (nonanone, cyclo-hexanone, acetophenone, 2-, 3-, and 4-methyleyclohexanone, p-methylacetophenone, benzyl methyl ketone, propiophenone, benzophenone) yielded by decarboxylation, a Schiff base which was hydrolyzed in 3N HCl to regenerate the ketone and to give the amine-HCl."
LaDecarbI.pdf