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US4177211A
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Process for the preparation of bis(aminophenyl)alkanes
Assignee: Pharmacia and Upjohn Co
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Filing: 1978-04-21
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Granted: 1979-12-04
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Expires: 1998-04-21
Abstract
Abstract An improved process is described for the preparation of bis(aminophenyl)alkanes which comprises heating the corresponding bis(di-alkoxyphenyl)alkane or corresponding cyclic ethers of bis(phenyl)alkanes with an at least stoichiometric proportion of an aniline acid addition salt, optionally in the presence of an inert organic solvent.
Inventors
- 👤 Kwok K. Sun
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:57
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; C07C; C07C209/00; C07C209/04; C07C209/14; C07C209/18; C07C209/64; C07C209/68; C07C41/00; C07C41/01; C07C41/18; C07C41/30
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
172 words
A process for the preparation of a bis(aminophenyl)alkane having the formula ##STR11## wherein R 1 and R 2 , taken individually, represent methyl and lower-alkyl, respectively, and R 1 and R 2 taken together with the C atom to which they are attached represent the residue of a 1,1-cycloalkylidene group having from 5 to 7 ring carbon atoms, inclusive; which process comprises reacting (a) the appropriately substituted bis(phenyl)alkane having the formula: ##STR12## wherein R 1 and R 2 have the significance defined above and A is a member selected from the class consisting of ##STR13## wherein R 3 and R 4 each represent lower alkoxy; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently selected from the group consisting of hydrogen and lower-alkyl; and n and m are integers from 0 to 1; with (b) at least 2 moles, per mole of said bis-(phenyl)alkane, of an aniline acid addition salt at a temperature in the range of 100° to 250° C.
Claim 2
Dependent Claim
172 words
A process for the preparation of a bis(aminophenyl)alkane having the formula ##STR11## wherein R 1 and R 2 , taken individually, represent methyl and lower-alkyl, respectively, and R 1 and R 2 taken together with the C atom to which they are attached represent the residue of a 1,1-cycloalkylidene group having from 5 to 7 ring carbon atoms, inclusive; which process comprises reacting (a) the appropriately substituted bis(phenyl)alkane having the formula: ##STR12## wherein R 1 and R 2 have the significance defined above and A is a member selected from the class consisting of ##STR13## wherein R 3 and R 4 each represent lower alkoxy; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently selected from the group consisting of hydrogen and lower-alkyl; and n and m are integers from 0 to 1; with (b) at least 2 moles, per mole of said bis-(phenyl)alkane, of an aniline acid addition salt at a temperature in the range of 100° to 250° C.
Claim 3
Dependent Claim
31 words
The process of claim 1 wherein said substituted bis(phenyl)alkane is 2,2-bis(2,4-dimethoxyphenyl)propane and the aniline acid addition salt is aniline hydrochloride whereby there is obtained 2,2-bis(4-aminophenyl)propane in the form of its dihydrochloride.
Claim 4
Dependent Claim
30 words
The process of claim 1 wherein said bis(phenyl)alkane is 2,2-bis(2,4-diethoxyphenyl)propane and the aniline acid addition salt is aniline hydrochloride whereby there is obtained 2,2-bis(4-aminophenyl)propane in the form of its dihydrochloride.
Claim 5
Dependent Claim
10 words
The process of claim 1 wherein the bis(phenyl)alkane is 10,10-isopropylidenebis(2,2,6,6-tetramethyl-dihydropyran[2,3-f]chroman).
Claim 6
Dependent Claim
19 words
The process of claim 1 wherein said reaction is carried out in the presence of an inert organic solvent.
Claim 7
Dependent Claim
23 words
The process of claim 1 wherein said reaction is carried out by heating the reactants in the absence of an inert organic solvent.
Claim 8
Dependent Claim
26 words
The process of claims 2 or 3 wherein said reaction is carried out at a pressure less than atmospheric and the 1,3-di-lower-alkoxybenzene by-product is recovered overhead.
Claim 9
Dependent Claim
43 words
A process which comprises heating together a 2,2-bis(2,4-di-loweralkoxyphenyl)propane and from 2 mole to 14 mole, per mole of the former, of aniline hydrochloride at a temperature of 100° C. to 250° C. whereby there is obtained 2,2-bis(4-aminophenyl)-propane in the form of its dihydrochloride.
Claim 10
Dependent Claim
43 words
A process which comprises heating together a 2,2-bis(2,4-di-loweralkoxyphenyl)propane and from 2 mole to 14 mole, per mole of the former, of aniline hydrochloride at a temperature of 100° C. to 250° C. whereby there is obtained 2,2-bis(4-aminophenyl)-propane in the form of its dihydrochloride.
Claim 11
Dependent Claim
19 words
The process of claim 8 wherein the heating is carried out in the presence of an inert orgaic solvent.
Claim 12
Dependent Claim
18 words
The process of claim 8 wherein the heating is carried out in the absence of an inert solvent.
Claim 13
Dependent Claim
24 words
The process of claim 8 wherein said reaction is carried out at a pressure less than atmospheric and the 1,3-di-lower-alkoxybenzene by-product is recovered overhead.
Claim 14
Dependent Claim
42 words
A process which comprises heating together 2,2-bis(2,4-dimethoxyphenyl)propane and from 2 mole to 14 mole, per mole of the former, of aniline hydrochloride at a temperature of 100° C. to 250° C. whereby there is obtained 2,2-bis(4-aminophenyl)-propane in the form of its dihydrochloride.
Claim 15
Dependent Claim
42 words
A process which comprises heating together 2,2-bis(2,4-dimethoxyphenyl)propane and from 2 mole to 14 mole, per mole of the former, of aniline hydrochloride at a temperature of 100° C. to 250° C. whereby there is obtained 2,2-bis(4-aminophenyl)-propane in the form of its dihydrochloride.
Claim 16
Dependent Claim
19 words
The process of claim 12 wherein the heating is carried out in the presence of an inert organic solvent.
Claim 17
Dependent Claim
18 words
The process of claim 12 wherein the heating is carried out in the absence of an inert solvent.
Claim 18
Dependent Claim
24 words
The process of claim 12 wherein said reaction is carried out at a pressure less than atmospheric and the 2,4-dimethoxybenzene by-product is recovered overhead.
References Cited (Backward Citations)
US3418371A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-03 | 1983-06-04 | 1983-12-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-03 | 1987-06-04 | 1987-12-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-03 | 1991-06-04 | 1991-12-04 | $7700.00 | Window Closed / Lapsed |