Heterocyclic amphoteric compounds

A mixture comprising at least two compounds having the formula 1:

• wherein
• R is a C3-C23 hydrocarbyl group;
• R1 is a C1-C8 hydrocarbyl group;
• HETN is a heterocyclic group selected from piperidine, pyridine, pyrollidine, quinoline, tetrahydroquinoline, indole, indoline, octahydroindole, acridine, octahydroacridine, and tetradecahydroacridine;
• X is O or NH;
• n is 0 or 1;
• and
• m is 0 or 1 and is chosen to afford a quaternary heterocyclic nitrogen, and
• wherein the at least two compounds have at least one different R substituent.

A process for preparing a compound having the formula 1:

• wherein
• R is a C3-C23 hydrocarbyl group;
• R1 is a C1-C8 hydrocarbyl group;
• HETN is a heterocyclic group selected from piperidine, pyridine, pyrollidine, quinoline, tetrahydroquinoline, indole, indoline, octahydroindole, acridine, octahydroacridine, and tetradecahydroacridine;
• X is O or NH;
• n is 0 or 1;
• and
• m is 0 or 1 and is chosen to afford a quaternary heterocyclic nitrogen,
• the process comprising:
• (a) contacting an acid or ester of formula 2 with a heterocyclic alcohol of formula 3 or a heterocyclic amine of formula 4:
• HO—(CH2)n—HETN—(R1)p 3
• H2N—(CH2)n—HETN—(R1)p 4
• in the presence of an enzyme at conditions effective to form an intermediate of formula 5:
• wherein
• R, R1, X, HETN, and n are as defined above,
• R4 is hydrogen or a C1-C6 alkyl group, and
• p is 0 or 1 and is chosen to afford a tertiary heterocyclic amine;
• and
• (b) contacting the intermediate of formula 5 with an acetic acid alkylating agent at conditions effective to form the compound of formula 1.

A process for preparing a mixture comprising at least two compounds having the formula 1:

• wherein
• R is a C3-C23 hydrocarbyl group;
• R1 is a C1-C8 hydrocarbyl group;
• HETN is a heterocyclic group selected from piperidine, pyridine, pyrollidine, quinoline, tetrahydroquinoline, indole, indoline, octahydroindole, acridine, octahydroacridine, and tetradecahydroacridine;
• X is O or NH;
• n is 0 or 1;
• and
• m is 0 or 1 and is chosen to afford a quaternary heterocyclic nitrogen, and
• wherein the at least two compounds have different R substituents,
• the process comprising:
• (a) contacting a mixture comprising at least two acids or esters of formula 2 with a heterocyclic alcohol of formula 3 or a heterocyclic amine of formula 4:
• HO—(CH2)n—HETN—(R1)p 3
• H2N—(CH2)n—HETN—(R1)p 4
• in the presence of an enzyme at conditions effective to form at least two intermediates of formula 5:
• wherein
• R, R1, X, HETN, and n are as defined above,
• R4 is hydrogen or a C1-C6 alkyl group,
• p is 0 or 1 and is chosen to afford a tertiary heterocyclic amine,
• the at least two acids or esters of the formula 2 have different R substituents, and
• the at least two intermediates of the formula 5 have different R substituents;
• and
• (b) contacting the intermediates of the formula 5 with an acetic acid alkylating agent at conditions effective to form the mixture of at least two compounds of the formula 1.