Alkylation of primary amines very often ends up with a significant amount of dialkylation products. Reductive amination with primary amines to give secondary amines does not proceed through the same mechanistic pathway, as the name says "reductive". Do you know what is reduced?
Alkylation of primary amines very often ends up with a significant amount of dialkylation products. Reductive amination with primary amines to give secondary amines does not proceed through the same mechanistic pathway, as the name says "reductive". Do you know what is reduced?
I have a carbonyl group and NH2R1 and the solvent NaBh3CN. By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
You mean you will form the imine first and then reduce it with the cyanoborohydride?
I have a carbonyl group and NH2R1 and the solvent NaBh3CN. By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
You mean you will form the imine first and then reduce it with the cyanoborohydride?
The reductive amination wants NaBh3CN, pH 6 to 7 and of course reagents. The method is used in the industry for making amines. The alkylation of amines is not very often used in the industry for making of amines and it has to do with the halogen reactivity. I think that making them in lab scale seems okay for both.
The solvent for reductive amination is friendly and pH conditions is not complicated. So i don't realy feel that one of the methods i to prefer over the other.
The reductive amination wants NaBh3CN, pH 6 to 7 and of course reagents. The method is used in the industry for making amines. The alkylation of amines is not very often used in the industry for making of amines and it has to do with the halogen reactivity. I think that making them in lab scale seems okay for both.
The solvent for reductive amination is friendly and pH conditions is not complicated. So i don't realy feel that one of the methods i to prefer over the other.
One cannot make a generalization like that. Even if one were to decide one method were better, I can assure you there would be instances in which the other method would be better.
One cannot make a generalization like that. Even if one were to decide one method were better, I can assure you there would be instances in which the other method would be better.
The carbonyl of choice and the NH2R1 group react and the NaBh3CN acts as reducing agent to form the amine, according to the mechanism scheme I am looking at. And then when the amine is formed i do workup (loss of hydrogen) to get a secondary amine. Is this wrong?
The carbonyl of choice and the NH2R1 group react and the NaBh3CN acts as reducing agent to form the amine, according to the mechanism scheme I am looking at. And then when the amine is formed i do workup (loss of hydrogen) to get a secondary amine. Is this wrong?
Not quite. NaBH3CN is not a solvent, its reducing agent (or it seems that yo think so from your previous post) The procedure is to mix the amine with aldehyde with acid catalyst if needed that will form the imine intermediate that can be isolated (doesnt have to be) and then you add the reducing agent to reduce the imine bond to get secondary amine.
There are also another methods to make secondary amines but there is not very much of them. My favourite is definitely olefin hydroamination with nitroarenes developed by Baran group but I didnt have the chance to try it in lab yet
Not quite. NaBH3CN is not a solvent, its reducing agent (or it seems that yo think so from your previous post) The procedure is to mix the amine with aldehyde with acid catalyst if needed that will form the imine intermediate that can be isolated (doesnt have to be) and then you add the reducing agent to reduce the imine bond to get secondary amine.
There are also another methods to make secondary amines but there is not very much of them. My favourite is definitely olefin hydroamination with nitroarenes developed by Baran group but I didnt have the chance to try it in lab yet
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I have a carbonyl group and NH2R1 and the solvent NaBh3CN. By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
I have a carbonyl group and NH2R1 and the solvent NaBh3CN. By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
It is making of a secondary amine by using reductive amination or using amine alkylation? Both methods seem nice and clean. Why would one method be less favorable? Is the solvent NaBh3CN not nice to work with? I thought that this solvent is nicer than NaBH4.
It is making of a secondary amine by using reductive amination or using amine alkylation? Both methods seem nice and clean. Why would one method be less favorable? Is the solvent NaBh3CN not nice to work with? I thought that this solvent is nicer than NaBH4.
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Reductive amination with primary amines to give secondary amines does not proceed through the same mechanistic pathway, as the name says "reductive".
Do you know what is reduced?
Reductive amination with primary amines to give secondary amines does not proceed through the same mechanistic pathway, as the name says "reductive".
Do you know what is reduced?
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VOTE
You mean you will form the imine first and then reduce it with the cyanoborohydride?
You mean you will form the imine first and then reduce it with the cyanoborohydride?
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The solvent for reductive amination is friendly and pH conditions is not complicated. So i don't realy feel that one of the methods i to prefer over the other.
The solvent for reductive amination is friendly and pH conditions is not complicated. So i don't realy feel that one of the methods i to prefer over the other.
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The procedure is to mix the amine with aldehyde with acid catalyst if needed that will form the imine intermediate that can be isolated (doesnt have to be) and then you add the reducing agent to reduce the imine bond to get secondary amine.
There are also another methods to make secondary amines but there is not very much of them. My favourite is definitely olefin hydroamination with nitroarenes developed by Baran group but I didnt have the chance to try it in lab yet
The procedure is to mix the amine with aldehyde with acid catalyst if needed that will form the imine intermediate that can be isolated (doesnt have to be) and then you add the reducing agent to reduce the imine bond to get secondary amine.
There are also another methods to make secondary amines but there is not very much of them. My favourite is definitely olefin hydroamination with nitroarenes developed by Baran group but I didnt have the chance to try it in lab yet
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This is a forum policy.
Click on the link near the top center of the forum page.
Forum Rules: Read This Before Posting.
This is a forum policy.
Click on the link near the top center of the forum page.
Forum Rules: Read This Before Posting.
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By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
By this reaction I will reduce the carbonyl with the NH2R1 group and solvent, to receive a imine intermediate and this will then give the secondary amine.
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