ES450304A1 - A process for the preparation of N-ciclohexil-N-methyl-N- (2-amino-3, 5-dibromobencil) -amine. (Machine-translation by Google Translate, not legally binding) - Google Patents
A process for the preparation of N-ciclohexil-N-methyl-N- (2-amino-3, 5-dibromobencil) -amine. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES450304A1 ES450304A1 ES450304A ES450304A ES450304A1 ES 450304 A1 ES450304 A1 ES 450304A1 ES 450304 A ES450304 A ES 450304A ES 450304 A ES450304 A ES 450304A ES 450304 A1 ES450304 A1 ES 450304A1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- amino
- preparation
- amine
- dibromobencil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- WMJWASKQHNPDBY-UHFFFAOYSA-N 1-bromo-3-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Br)C=CC=C1CBr WMJWASKQHNPDBY-UHFFFAOYSA-N 0.000 abstract 1
- NRLRAEIGVPJEGG-UHFFFAOYSA-N 2-bromo-6-[[cyclohexyl(methyl)amino]methyl]aniline Chemical compound C1CCCCC1N(C)CC1=CC=CC(Br)=C1N NRLRAEIGVPJEGG-UHFFFAOYSA-N 0.000 abstract 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 abstract 1
- 230000001684 chronic effect Effects 0.000 abstract 1
- XSHMUYDEXIKAPP-UHFFFAOYSA-N n-[(3-bromo-2-nitrophenyl)methyl]-n-methylcyclohexanamine Chemical compound C1CCCCC1N(C)CC1=CC=CC(Br)=C1[N+]([O-])=O XSHMUYDEXIKAPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
For the preparation of N-cyclohexyl-N-methyl-N-(2-amino-3,5-dibromobenzyl)amine, 3-bromo-2-nitrobenzyl bromide is used as a starting substance and is reacted with N-methylcyclohexylamine in the presence of an acid acceptor. The nitro group of the resultant N-cyclohexyl-N-methyl- 2-nitro-3-bromobenzylamine is then reduced and the resulting N-cyclohexyl-N-methyl-2-amino-3-bromobenzylamine is brominated. This process enables the preparation of this compound in a simple manner with a yield of more than 80%. The compound has excellent bronchosecretolytic action and can be used in the therapy of chronic, non-specific disorders of the airways.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002384 | 1975-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES450304A1 true ES450304A1 (en) | 1977-10-01 |
Family
ID=10995655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES450304A Expired ES450304A1 (en) | 1975-10-28 | 1976-07-30 | A process for the preparation of N-ciclohexil-N-methyl-N- (2-amino-3, 5-dibromobencil) -amine. (Machine-translation by Google Translate, not legally binding) |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5253836A (en) |
| AT (1) | AT351504B (en) |
| CH (1) | CH622488A5 (en) |
| CS (1) | CS199633B2 (en) |
| DE (1) | DE2633518A1 (en) |
| DK (1) | DK145293C (en) |
| ES (1) | ES450304A1 (en) |
| FI (1) | FI64351C (en) |
| PL (1) | PL103750B1 (en) |
| SE (1) | SE415654B (en) |
| SU (1) | SU580829A3 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5848872U (en) * | 1981-09-30 | 1983-04-02 | 松下電工株式会社 | Folding door hinge structure |
| JPS61139688U (en) * | 1985-02-18 | 1986-08-29 | ||
| JPS61206065U (en) * | 1985-06-15 | 1986-12-26 | ||
| DE19529432C1 (en) * | 1995-08-10 | 1997-05-15 | Boehringer Ingelheim Kg | Process for the preparation of benzylamine derivatives |
-
1976
- 1976-07-19 CH CH935976A patent/CH622488A5/en not_active IP Right Cessation
- 1976-07-20 SE SE7608246A patent/SE415654B/en unknown
- 1976-07-23 AT AT544276A patent/AT351504B/en not_active IP Right Cessation
- 1976-07-26 DE DE19762633518 patent/DE2633518A1/en not_active Withdrawn
- 1976-07-27 FI FI762141A patent/FI64351C/en not_active IP Right Cessation
- 1976-07-28 CS CS764956A patent/CS199633B2/en unknown
- 1976-07-30 SU SU7602386749A patent/SU580829A3/en active
- 1976-07-30 DK DK346376A patent/DK145293C/en active
- 1976-07-30 PL PL1976191536A patent/PL103750B1/en unknown
- 1976-07-30 ES ES450304A patent/ES450304A1/en not_active Expired
- 1976-07-30 JP JP51091253A patent/JPS5253836A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU580829A3 (en) | 1977-11-15 |
| FI64351C (en) | 1983-11-10 |
| JPS5616786B2 (en) | 1981-04-18 |
| CS199633B2 (en) | 1980-07-31 |
| PL103750B1 (en) | 1979-07-31 |
| JPS5253836A (en) | 1977-04-30 |
| FI762141A (en) | 1977-04-29 |
| DE2633518A1 (en) | 1977-05-12 |
| DK145293C (en) | 1983-03-14 |
| SE7608246L (en) | 1977-04-29 |
| DK346376A (en) | 1977-04-29 |
| SE415654B (en) | 1980-10-20 |
| FI64351B (en) | 1983-07-29 |
| ATA544276A (en) | 1978-01-15 |
| AT351504B (en) | 1979-07-25 |
| DK145293B (en) | 1982-10-25 |
| CH622488A5 (en) | 1981-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19980302 |