US4089853A
Expired / Lapsed
US
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Process for the preparation of cis-5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)-ethyl]indoline
Assignee: Wyeth Holdings LLC
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Filing: 1977-02-09
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Granted: 1978-05-16
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Expires: 1997-02-09
Abstract
Abstract There is provided a process for the manufacture of pure cis isomer of 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline by the ionic hydrogenation of 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indole.
Inventors
- 👤 Anthony Edward Lanzilotti
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 00:13
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
92 words
A process for the preparation of cis-5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline which comprises ionically hydrogenating 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indole with a hydrogenation pair consisting essentially of a proton donor selected from the group consisting of concentrated phosphoric acid, concentrated sulfuric acid, trifluoroacetic acid and polyphosphoric acid and a hydride ion donor selected from the group consisting of di(alkyl C 1 -C 3 )silanes, tri(alkyl C 1 -C 3 )silanes, diphenylsilane and triphenylsilane at a temperature of from about 25° to about 65° C. for a period of time sufficient for a substantial degree of Δ 2 -hydrogenation to occur.
Claim 2
Dependent Claim
92 words
A process for the preparation of cis-5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline which comprises ionically hydrogenating 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indole with a hydrogenation pair consisting essentially of a proton donor selected from the group consisting of concentrated phosphoric acid, concentrated sulfuric acid, trifluoroacetic acid and polyphosphoric acid and a hydride ion donor selected from the group consisting of di(alkyl C 1 -C 3 )silanes, tri(alkyl C 1 -C 3 )silanes, diphenylsilane and triphenylsilane at a temperature of from about 25° to about 65° C. for a period of time sufficient for a substantial degree of Δ 2 -hydrogenation to occur.
Claim 3
Dependent Claim
22 words
A process according to claim 1 wherein the proton donor is trifluoroacetic acid and the hydride ion donor is trimethylsilane or triethylsilane.
References Cited (Backward Citations)
US3188313A
Cited
US3751416A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-15 | 1981-11-14 | 1982-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-15 | 1985-11-14 | 1986-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-15 | 1989-11-14 | 1990-05-16 | $7700.00 | Window Closed / Lapsed |