WO2000032601A2 - Process for preparing cross-bridged tetraaza macrocycles - Google Patents

Process for preparing cross-bridged tetraaza macrocycles Download PDF

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Publication number
WO2000032601A2
WO2000032601A2 PCT/US1999/027316 US9927316W WO0032601A2 WO 2000032601 A2 WO2000032601 A2 WO 2000032601A2 US 9927316 W US9927316 W US 9927316W WO 0032601 A2 WO0032601 A2 WO 0032601A2
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hgand
tetraaza
macrocychc
process
formula
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PCT/US1999/027316
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French (fr)
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WO2000032601A3 (en
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George Douglas Ii Hiler
Christopher Mark Perkins
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The Procter & Gamble Company
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Publication of WO2000032601A3 publication Critical patent/WO2000032601A3/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00Compounds containing elements of Groups 7 or 17 of the Periodic System
    • C07F13/005Compounds without a metal-carbon linkage
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B01J31/182Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08Bridged systems
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72Manganese
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96Water

Abstract

The present invention relates to a process for preparing a cross-bridged tetraaza macrocyclic ligand having formula (I) wherein each R is independently C1-C8 linear or branched alkyl, -(CH2)xCO2M, and mixtures thereof; provided both of the R units are not methyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; by contacting a di-quaternary cis tetracycle precursor with hydrogen in the presence of a palladium catalyst in an aqueous solution having a pH of at least about 10 at a temperature of about 40 °C to about 100 °C.

Description

PROCESS FOR PREPARING CROSS-BRIDGED TETRAAZA MACROCYCLES

FIELD OF THE INVENTION The present invention relates to an improved process for preparing cross-bridged tetraaza macrocycles, said macrocycles suitable as ligands for use m preparing transition metal complexes The present invention provides a process which is well suited for use in industrial and other commercial preparations of the herein described crossed-bπdged macrocycles.

BACKGROUND OF THE INVENTION Tetraaza macrocyclics, for example, cyclam, have been prepared in numerous ways, however, there is a paucity of information relating to the preparation of cross-bridged tetraaza macrocyclics inter aha bis N-substituted tetraaza macrocyclics inter alia 5,12 dialkyl 1,5,8,12- tetraaza-bιcyclo[6.6.2]hexadecanes which have recently found wide applicability as ligands especially in the area of transition metal catalysts inter alia bleach catalysts.

WO 98/39335 Al "Improved Methods of Making Cross-Bridged Macropoly-cycles" discloses a rational procedure for preparing cross bridged macropolycychc ligands which is amenable to high yields necessary for industrial scale-up. However, the reductive ring cleavage step which results in bicyclo bridged-ring formation utilizes a borohydπde reducing agent. This type of reducing agent can place constraints on the formulator. For example, the need to break up the amine/borohydπde complex duπng work-up and the proper recovery and disposal of boron waste products adds cost to the process. Also, if excess borohydπde is needed, this requires neutralization which involves the use of acid and the evolution of large quantities of hydrogen gas.

Therefore, a need exists for a highly quantitative, preferably catalytic, process for preparing cross-bridged macropolycychc ligands which is adaptable to either continuous flow processes or batch preparations.

SUMMARY OF THE INVENTION The present invention meets the aforementioned needs m that it has been surprisingly discovered that select bis N-substituted tetraaza macrocyclics can be converted to cross-bridged macropolycychc ligands via catalytic hydrogenation. A first aspect of the present invention relates to a process for preparing a tetraaza macrocychc hgand having the formula:

Figure imgf000004_0001
wherein each R is independently Cj-Cg linear or branched alkyl, -(CH2)xC02M, and mixtures thereof, preferably both of the R units are not methyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; said process comprising the steps of a) hydrogenat g a tetraaza macrocychc hgand precursor having the formula:

Figure imgf000004_0002
wherein X is an anion which provides charge neutrality, with from about 1 ppm of a transition metal hydrogenation catalyst at a pH of at least 8 to form a tetraaza macrocychc hgand; and b) optionally isolating said hgand.

These and other objects, features, and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims. All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C) unless otherwise specified. All documents cited are in relevant part, incorporated herein by reference.

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the catalytic hydrogenation of tetraaza macrocycles having the formula:

Figure imgf000005_0001
wherein the covalent bond between the N-substituted quaternary ring nitrogen and the bridging carbon is broken and a cross-bridged macrocychc hgand having the formula:

Figure imgf000005_0002
is the resulting product.

In the above formula each R is independently Cj-C8 linear or branched alkyl, - (CH2)sC02M, and mixtures thereof, preferably both of the R units are not methyl; more preferably one R unit is methyl and the other R unit is selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl. and mixtures thereof; of the methyl/alkyl R unit mixtures preferably one R is methyl and the other R is ethyl or propyl. A most preferred hgand consists of a unit wherein one R unit is methyl and the other R unit is ethyl. A preferred gand is a macrocychc ring wherein each R unit is ethyl. M is hydrogen or a salt forming cation, non-limiting examples of which are sodium, potassium, calcium, ammonium. When R is -(CH2)xC02M the index x has the value from 1 to about 6. preferably x is 1. The index n defines the size of the macrocychc ring. The index n has the value of from 0 to about 3. A preferred macrocychc ring has one opposite set of n indices equal to 1 and the other set of n indices equal to 0 as in the general formula:

Figure imgf000006_0001
wherein R is the same as defined herein above.

Preferred ligands according to the present invention comprise R unit pairs which are selected from the group consisting of methyl and ethyl, di ethyl, methyl and propyl, ethyl and propyl, methyl and butyl, ethyl and butyl, and mixtures thereof.

The starting materials for the process of the present invention are tetraaza macrocychc hgand precursors, or alternatively, bis-quaternary as tetracycles, having the formula-

Figure imgf000006_0002
wherein R and n are the same as defined herein above. X is an anion which serves to provide electronic neutrality to the bis-quaternary cis tetracycle. Those of ordinary skill in the art recognize that the term "electronic neutrality" refers to "a sufficient amount of an anionic species which satisfies the molecular charge balance requirements" and that a mixture of mono-, di-, tri-. etc. electronic species may be use herein. X preferably has unit negative charge, for example, halogen, tosylate, methylsulfate, ethylsulfate. However, X may have more than one negative charge, for example, sulfate, in which case the formulator requires only half the amount necessary when using a unit negative-charged anion. Preferred X is chloride, bromide, iodide, sulfate, ethyl sulfate, methyl sulfate, tosylate, mesylate, triflate, and mixtures thereof.

STEP (a) Hydrogenation - Reductive Cleavage

Step (a) comprises the reductive cleavage via catalytic hydrogenation as outlined in the following scheme'

Figure imgf000007_0001

wherein the -tetracycle bis quaternary salt is converted to the cross-bridged tetraaza macrocycle. Step (a) is conducted in the presence of a catalyst, preferably a supported catalyst. Non- hmiting examples of catalysts include platinum on carbon, palladium on carbon (Pd/C), palladium hydroxide on carbon (Pd(OH)2/C), rhodium on carbon (Rh/C), Raney nickel, and mixtures thereof. A preferred catalyst is Pd(0H) /C. The supported catalysts may comprise from about 1% to about 50% by weight of transition metal, however, the pure metal, i.e. palladium, can be used without the need for a "support", i.e., carbon. A "catalytic amount" of catalyst is sufficient to provide the reduction of step (a). For the purposes of the present invention the term catalytic amount is defined as "from about 1 ppm of a 5% by weight transition metal catalyst". However, the formulator, due to poisoning of the catalyst surface by reaction products may use more than a catalytic amount of a catalyst. The amount of catalyst used in step (a) of the present invention is preferably from about 10 ppm of a catalyst which contains from about 5% to 50% by weight, of a transition metal, more preferably from about 100 ppm, yet more preferably from about 0.1% by weight, of a transition metal supported catalyst A reaction solution which comprises 0.1% by weight, of a transition metal supported catalyst, said catalyst comprising, for example, 10% by weight of palladium on carbon, has 0.01% transition metal or 100 ppm transition metal present.

The amount of hydrogen gas present in step (a) of the present invention need only be enough to sufficiently saturate the catalyst surface, preferably the hydrogen pressure is from 200 psi, more preferably from 400 psi, most preferably from 800 psi to about 2000 psi, more preferably to 1000 psi. Step (a) of the present process can be conducted at a temperature of from 20° C, preferably from about 40° C, more preferably from about 60° C to about 100° C, preferably to about 90° C, more preferably to about 80° C, most preferably to about 65° C. The pH under which Step (a) must be conducted is at least 8, preferably at least 10, more preferably at least about 11. Preferably the base which is used to adjust the pH is in the form of an aqueous solution. Preferred bases are selected from the group consisting of potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, and mixtures thereof. As a non-limiting example, it is satisfactory to use a sufficient amount of 1 M (molar) aqueous base to adjust the pH to the required level. A convenient and preferred base is potassium carbonate.

As a suitable alternative, Step (a) can be conducted in the presence of a solvent other than water, or m the absence of water. A mixture of a suitable solvent and water is a suitable means for conducting the hydrogenation process of the present invention. In the case where water is absent, sufficient base must be present to stabilize the transition state of the reactants and products during hydrogenation. Non-limiting examples of solvents include methanol, ethanol, n- propanol, isopropanol, N.N-dimethyl formamide, n-butanol. iso-butanol, tert-butanol, and mixtures thereof; preferred solvents are selected from the group consisting of ethanol, n- propanol, N,N-dιmethyl formamide, and mixtures thereof. When a solvent is present and the base is in the form of an aqueous solution, the ratio of said volume of an aqueous base, to said solvent is from about 1 : 10 to about 1 : 1, preferably the ratio of the volume of aqueous base to solvent is 1 :4. It is desirable, but not a requirement, that the aqueous base and solvent form a two phase system.

The process of the present invention comprises an optional, although preferred, Step (b) which is an isolation step. Typically this step involves filtration of the reaction solution to remove the catalyst. In addition, this step may comprise a neutralization step, however, the product can be isolated or removed from the reaction matrix in any manner which the formulator desires.

When filtration of the catalyst is a desired step, the reaction solution containing the cross- bridged hgand is filtered to remove the catalyst to form a crude filtrate. This crude filtrate can be neutralized or the tetraaza macrocychc hgand can be isolated by extraction or crystallization directly from the preferably aqueous solution.

Steps (a) and (b) and any optional extensions thereto, for example, a crystallization step, a solvent drying step, a purging step, may be suitably adapted for either batch processes or continuous processes, for example, continuous flow processes. As mentioned herein, the process of the present invention may compπse other optional steps as deemed necessary and/or desirable by the formulator. These optional steps may include but are not limited to, pre-saturation of the catalyst with hydrogen, drawing a vacuum on the system, and recovery of the catalyst and solvents. Preferably the ligands formed by the process of the present invention are converted into manganese containing transition metal catalysts in a subsequent, however optional, process step The bleach catalysts comprise a central manganese atom and a cross-branched hgand formed by the process of the present invention. The final bleach catalyst may comprise one or more other compatible ligands inter aha chlorine atom. The preferred catalysts are suitable as bleaching agents.

The following is a non-hmitmg example of the process of the present invention.

Preparation of 5,12-diethyl-l ,5,8,12-tetraaza-bicvclo [6.6.21 hexadecane To a thick walled, glass autoclave sleeve is added the bis-quaternary as tetracycle having the formula:

Figure imgf000009_0001

(3.0 g, 6.8 mmol) and a 1M aqueous solution of K2C03 (30 mL). The solution is agitated to dissolve the substrate then 20% Pd(OH)2/carbon (0.7 g, 1.0 mmol) is added. The glass sleeve is placed into a rocking autoclave and hydrogenated at 65° C with 1900 psig hydrogen for 4 hours. The reaction is cooled and the solution filtered through glass fiber filter paper to remove the catalyst and the filtrate is reduced to a white solid under vacuum The white solid is suspended in refluxmg ethanol and the un-dissolved inorganic salts are collected by filtration. After concentrating the filtrate under vacuum, the resulting oily residue is dissolved in aqueous 4M KOH (4 mL) and extracted three times with 25 mL portions of toluene. The toluene extracts are combined and concentrated in vacuo to afford 5,12-dιethyl-l,5,8,12-tetraaza- bιcyclo[6.6.2]hexadecane (1.56 g) in 81% yield as a clear oil.

The following is an example of an optional, but preferred step of the process of the present invention which is conversion to a manganese transition metal bleach catalyst. Preparation of dichloro 5,12-diethyl-l,5,8,12-tetraaza- bicvclo [6.6.21 hexadecane manganese To a 100 mL reaction flask is charged anhydrous acetonitπle (50 mL) and 5,12-dιethyl- l,5,8,12-tetraaza-bιcyclo[6.6.2]hexadecane (1 4 g, 5 mmol). The resulting suspension is degassed under vacuum with subsequent re-filhng with argon. This process is repeated six times Manganese(II) chloride (0.590 g, 4.7 mmol) is added and the reaction is refluxed for 3 hours The resulting solution is filtered through glass-fiber filter paper. The resulting filtrate is concentrated under reduced pressure at 45° C to afford a solid. The solid is suspended in toluene (50 mL) and the resulting dark supernatant is discarded. Treatment with toluene is repeated five times. The resulting solid is dried under vacuum to yield dichloro 5,12-dιethyl-l,5,8,12-tetraaza- bιcyclo[6.6.2]hexadecane manganese (1.48 g, 73% yield).

Claims

WHAT IS CLAIMED IS :
A process for preparing a tetraaza macrocychc hgand having the formula:
Figure imgf000011_0001
wherein each R is independently C C8 linear or branched alkyl, -(CH2) C02M, and mixtures thereof, provided both of the R units are not methyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; said process comprising the steps of: a) hydrogenating a tetraaza macrocychc hgand precursor having the formula:
Figure imgf000011_0002
wherein X ' is an anion which provides charge neutrality, with from 1 ppm of a transition metal hydrogenation catalyst at a pH of at least 8 to form a tetraaza macrocychc hgand; and b) optionally isolating said hgand.
2. A process according to Claim 1 wherein said transition metal hydrogenation catalyst is selected from the group consisting of platinum, palladium, palladium hydroxide, rhodium, Raney nickel, and mixtures thereof.
A process according to either of Claims 1 or 2 wherein step (a) is conducted at a temperature of from 40° C to 100° C, at a pH of at least 10, and in the presence of a solvent, said solvent selected from the group consisting of water, N,N-dιmethyl formamide, methanol. ethanol, isopropanol, n-butanol, iso-butanol, tert-butanol, and mixtures thereof.
4. A process according any of Claims 1-3 wherein said precursor has the formula:
Figure imgf000012_0001
wherein R and X are the same as defined herein above.
5. A process according to any of Claims 1-4 wherein each R is ethyl.
6. A process according to any of Claims 1-5 wherein one R is methyl and one R is ethyl.
A process for preparing a tetraaza macrocychc hgand having the formula:
Figure imgf000012_0002
wherein one R unit is methyl and the other R unit is selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl, and mixtures thereof; said process comprising the steps of: a) hydrogenating a tetraaza macrocychc hgand precursor having the formula:
Figure imgf000013_0001
wherein X " is an anion which provides charge neutrality, with from 1 ppm of a palladium hydrogenation catalyst at a pH of at least 10 to form a tetraaza macrocychc hgand; and b) optionally isolating said hgand.
A process for preparing a tetraaza macrocychc hgand having the formula:
Figure imgf000013_0002
wherein each R is independently C C8 linear or branched alkyl, -(CH2) C02M, and mixtures thereof, provided both of the R units are not methyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; said process compπsmg the steps of: a) hydrogenating a tetraaza macrocychc hgand precursor having the formula:
Figure imgf000013_0003
wherein X " is an anion which provides charge neutrality, with from 1 ppm of a palladium hydrogenation catalyst, said palladium catalyst selected from the group consisting of supported palladιum(O). palladium hydroxide, and mixtures thereof; at a pH of at least 8; in the presence of a solvent, said solvent selected from the group consisting of water, methanol, ethanol, N,N-dιmethyl formamide, n-butanol, iso-butanol, tert-butanol, and mixture thereof, at a temperature of from 0° C to 100° C; to form a tetraaza macrocychc hgand; and b) removing the catalyst by filtration to form a crude filtrate: c) optionally isolating said hgand by crystallizing, extracting, distilling, or other suitable means.
A process according to Claim 8 wherein said process further comprises the step of treating said hgand with manganese to form a cross-bridged tetraaza macrocychc transition metal catalyst.
A process for preparing a tetraaza macrocychc hgand having the formula:
Figure imgf000014_0001
wherein R units are R unit pairs selected from the group consisting of methyl and ethyl, diethyl, methyl and propyl, ethyl and propyl, methyl and butyl, ethyl and butyl, and mixtures thereof; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; said process composing the steps of: a) hydrogenatmg a tetraaza macrocychc hgand precursor having the formula:
Figure imgf000014_0002
wherein X " is an anion which provides charge neutrality, with from 1 ppm of a transition metal hydrogenation catalyst at a pH of at least 8 to form a tetraaza macrocychc hgand; and b) optionally isolating said hgand.
11. A transition metal catalyst comprising: a) a crossed-bπdged hgand having the formula:
Figure imgf000015_0001
wherein each R is independently C C8 linear or branched alkyl, -(CH2)χC02M, and mixtures thereof, provided both of the R units are not methyl or butyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from O to 3; b) manganese; and c) optionally one or more compatible ligands.
12. A compound according to Claim 11 having the formula:
Figure imgf000015_0002
PCT/US1999/027316 1998-11-30 1999-11-18 Process for preparing cross-bridged tetraaza macrocycles WO2000032601A2 (en)

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EP19990963923 EP1135392A2 (en) 1998-11-30 1999-11-18 Process for preparing cross-bridged tetraaza macrocycles
AU20261/00A AU2026100A (en) 1998-11-30 1999-11-18 Process for preparing cross-bridged tetraaza macrocycles
JP2000585243A JP2002531457A (en) 1998-11-30 1999-11-18 Method of manufacturing a cross-linked tetra-aza macrocycles such
CA 2348893 CA2348893A1 (en) 1998-11-30 1999-11-18 Process for preparing cross-bridged tetraaza macrocycles

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