(R)-N-Benzyl-N-(1-phenylethyl)cyclohexanamine

Round 1

Reviewer 1 Report

In this short note Narciso M. Garrido and co-workers prepared and characterized (R)-N-benzyl-N-(1-phenylethyl)cyclohexanamine but the introduction and manuscript is poorly written and has several typos. I highly recommend the authors to edit the language and correct spelling mistakes prior to acceptance.

Line 12: Previous

Line 13: Unsaturated not insaturated

Line 15: Random usage of upper case and lower cases “High Resolution Mass Spectrometry and infrared spectroscopy”

Line 95: solid not Solido, pale yellow would be more appropriate

Line 113: synthetized

Author Response

Dear Reviewer,

Thank you so much for your guidelines in reviewing our manuscript, the following changes have been introducing accordingly to your comments:

Referee: I highly recommend the authors to edit the language and correct spelling mistakes prior to acceptance.

Author´s answer: The language review has been carried out by experts and in our opinion the new version is improved and expresses the objectives of the work more clearly.

Referee: Line 12: Previous

Line 13: Unsaturated not insaturated

Line 15: Random usage of upper case and lower cases “High Resolution Mass Spectrometry and infrared spectroscopy”

Line 95: solid not Solido, pale yellow would be more appropriate

Line 113: synthetized

Author´s answer: All these typos have been corrected.

Reviewer 2 Report

This article “(R)-N-benzyl-N-(1-phenylethyl)cyclohexanamine” reported the synthesis of titled compound via Michael addition, ester hydrolysis and decarboxylation reaction. Indeed, as the authors claimed the chiral dibenzylamine synthesis and its derivatives are a class of compound with highly biological activities. 

Herein, the chiral product was obtained with high yield and fully characterized with 1H NMR, 13C NMR, DEPT, HSQC, HMBC, COSY, HRMS, as well as IR. Moreover, the manuscript is well-written and well-organized. This reviewer recommends its publication on Molbank after minor revision. 

There are some typos. Line 13, “insaturated” should be “unsaturated”. Line 21, “usefull” should be “useful”.

“Figure 1”, “Figure 2” would be better with “Scheme 1”, “Scheme 2”.

Figure 2, please add the reaction conditions of "a" in the legend.

A general comment: it is a pity that two newly generated chiral centers were neutralized after decarboxylation. It would be more interesting to acquire its derivatives with the retention of the two chiral centers.

Author Response

Dear Reviewer,

Thank you so much for your guidelines in reviewing our manuscript, the following changes have been introducing accordingly to your comments:

Referee: There are some typos. Line 13, “insaturated” should be “unsaturated”. Line 21, “usefull” should be “useful”.

Author´s answer: All these typos have been corrected.

Referee: “Figure 1”, “Figure 2” would be better with “Scheme 1”, “Scheme 2”.

Author´s answer: It has been corrected.

Referee: Figure 2, please add the reaction conditions of "a" in the legend.

Author’s answer: The reaction conditions have been added.

Referee: A general comment: it is a pity that two newly generated chiral centers were neutralized after decarboxylation. It would be more interesting to acquire its derivatives with the retention of the two chiral centers.

Author’s answer: We totally agree with the opinion of the reviewer but our intention is the synthesis of amines by decarboxylation and the methodology can be extended to complex molecules from accessible alpha,beta unsaturated esters that could maintain stereogenic centers on the starting material and that created in the amine insertion. Likewise, when addition/alkylation tandem reaction is carried out, in the decarboxylation the two new stereocenters can be maintained, without compromising any of them.

In this article we have proven the synthetic feasibility of the process, although unfortunately the two stereocenters created have been lost in the objective but the potential for the synthesis of important amines is maintained.