Salts of diaminoacetals and diaminoketals and their synthesis, and their transformations to diaminoacetals and diaminoketals
This application relates, in part, to novel salts represented by the following structure of Formula (1): wherein R 1a is selected from the group consisting of hydrogen and optionally substituted alkyl (e.g., unsubstituted C 1-6 alkyl, e.g., —CH 3 ); R 1b is optionally substituted alkyl (e.g., unsubstituted C 1-6 alkyl, e.g., —CH 3 ); each occurrence of R 2 and R 3 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, and optionally substituted aryl; R 2 and R 3 can combine with each other to form optionally substituted cycloalkyl; each m and n is independently an integer ranging from 1 to 20 (e.g., m and n is independently an integer ranging from 1 to 5); and each of Q 1⊖ and Q 2⊖ is independently a counterion (e.g., each of Q 1⊖ and Q 2⊖ is independently a counterion selected from the group consisting of chloride, bromide, fluoride, iodide, acetate, carboxylate, hydrogen sulfate, nitrate, and phenolate, and sulfonate, e.g., chloride), and methods of making the same.
1. A process for preparing a salt of a compound represented by Formula (2-1):
wherein
R 1a is selected from the group consisting of hydrogen and optionally substituted alkyl;
R 1b is optionally substituted alkyl;
each occurrence of R 2 and R 3 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl;
or
optionally substituted aryl, or R 2 and R 3 can combine with each other to form optionally substituted cycloalkyl; and
each instance of n is the same integer ranging from 1 to 20,
the process comprising the reaction of an aldehyde equivalent or ketone equivalent with a salt of a compound represented by Formula (3) to produce the salt of the compound of Formula (2-1):
2. The process of claim 1 , wherein each n is 2.
3. The process of claim 1 , wherein the salt of the compound represented by Formula (2-1) is a salt represented by Formula (1-1):
wherein
R 1a is selected from the group consisting of hydrogen and optionally substituted alkyl;
R 1b K is optionally substituted alkyl;
each occurrence of R 2 and R 3 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, and optionally substituted aryl, or
R 2 and R 3 can combine with each other to form optionally substituted cycloalkyl;
each n is an integer ranging from 1 to 20; and
each of Q 1⊖ and Q 2⊖ is independently a counterion.
4. The process of claim 3 , wherein Q 1⊖ and Q 2⊖ are both chloride.
5. The process of claim 1 , wherein the salt of the compound represented by Formula (2-1) is a salt of the compound represented by Formula (1-a-II):
6. The process of claim 1 , wherein the salt of the compound represented by Formula (2-1) is a salt of the compound represented by Formula (1-a-II):
wherein R 2 is unsubstituted C 1-6 alkyl and R 1a is independently selected from the group consisting of hydrogen and —CH 3 .
7. The process of claim 1 , wherein the ketone equivalent is selected from the group consisting of 2,2-dimethoxypropane, 2-methoxypropene, 2,2-diethoxypropane; and 2-ethoxypropene.
8. The process of claim 7 , wherein the ketone equivalent is selected from the group consisting of 2,2-dimethoxypropane and 2-methoxypropene.
9. The process of claim 8 , wherein the ketone equivalent is 2,2-dimethoxypropane.
10. The process of claim 8 , wherein the ketone equivalent is 2-methoxypropene.
11. The process of claim 1 , wherein the aldehyde equivalent is selected from the group consisting of 1,1-dimethoxyethane; methyl vinyl ether, 1,1-diethoxyethane, and ethyl vinyl ether.
12. The process of claim 1 , wherein the salt of the compound of Formula (3) is selected from the group consisting of:
13. The process of claim 1 , further comprising contacting the salt of the compound of Formula (1-1) with a base to produce the compound of Formula (2-1).
14. The process of claim 6 , wherein the compound of Formula (2-1) is selected from the group consisting of:
15. The process of claim 1 , wherein the reaction is carried out in the presence of a solvent.
16. The process of claim 1 , wherein the compound of Formula (2) is represented by:
17. The process of claim 1 , wherein the compound of Formula (2) is represented by: