DE2337931A1 - Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin - Google Patents
Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylaminInfo
- Publication number
- DE2337931A1 DE2337931A1 DE19732337931 DE2337931A DE2337931A1 DE 2337931 A1 DE2337931 A1 DE 2337931A1 DE 19732337931 DE19732337931 DE 19732337931 DE 2337931 A DE2337931 A DE 2337931A DE 2337931 A1 DE2337931 A1 DE 2337931A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- dibromo
- tricyclohexyl
- trimethyl
- phosphoric acid
- 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.)
- Pending
Links
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title description 12
- 235000019445 benzyl alcohol Nutrition 0.000 title description 4
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 title description 2
- PAYDUUFACYKFRI-UHFFFAOYSA-N n-bis[cyclohexyl(methyl)amino]phosphoryl-n-methylcyclohexanamine Chemical compound C1CCCCC1N(C)P(=O)(N(C)C1CCCCC1)N(C)C1CCCCC1 PAYDUUFACYKFRI-UHFFFAOYSA-N 0.000 title description 2
- 229960004217 benzyl alcohol Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- GHUMSGGCKVMYGH-UHFFFAOYSA-N (2-amino-3,5-dibromophenyl)methanol Chemical compound NC1=C(Br)C=C(Br)C=C1CO GHUMSGGCKVMYGH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RCPAZWISSAVDEA-UHFFFAOYSA-N 2-amino-3,5-dibromobenzaldehyde Chemical compound NC1=C(Br)C=C(Br)C=C1C=O RCPAZWISSAVDEA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WFIPYARNKIWELZ-UHFFFAOYSA-N n-[bis(methylamino)phosphoryl]methanamine Chemical compound CNP(=O)(NC)NC WFIPYARNKIWELZ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337931 DE2337931A1 (de) | 1973-07-26 | 1973-07-26 | Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin |
| FI1776/74A FI177674A (ja) | 1973-07-26 | 1974-06-11 | |
| AT510674A AT330739B (de) | 1973-07-26 | 1974-06-20 | Verfahren zur herstellung von 2-amino -n- cyclohexyl -3,5- dibrom -n- methyl-benzylamin sowie von seinen saureadditionssalzen |
| CS4467A CS170115B2 (ja) | 1973-07-26 | 1974-06-25 | |
| CS7500001285A CS184839B2 (en) | 1973-07-26 | 1974-06-25 | Method for producing triamide of n,n',n''-tricyclohexyl-n,n',n''-trimethyl phosphoric acid |
| BG7400031992A BG24231A3 (en) | 1973-07-26 | 1974-06-28 | Method of preparing triamide of n,n,n-tricyclohexyl-n,n,n-trimethylphosphoric acid |
| ES427954A ES427954A1 (es) | 1973-07-26 | 1974-07-04 | Procedimiento para la preparacion de 2-amino - n - ciclohe-xil-3,5-dibromo - n - metil-bencilamina. |
| NL7409046A NL7409046A (nl) | 1973-07-26 | 1974-07-04 | Werkwijze ter bereiding van 2-amino-n-cyclo- hexyl-3,5-dibroom-n-methylbenzylamine. |
| DK397274A DK135837C (da) | 1973-07-26 | 1974-07-23 | Fremgangsmade til fremstilling af n-cyclohexyl-n-methyl-(2-amino-3,5-dibrombenzyl)amin |
| CH1023574A CH597147A5 (ja) | 1973-07-26 | 1974-07-24 | |
| HUTO972A HU167868B (ja) | 1973-07-26 | 1974-07-24 | |
| HUTO1000A HU168460B (ja) | 1973-07-26 | 1974-07-24 | |
| PL1974173005A PL94273B1 (ja) | 1973-07-26 | 1974-07-25 | |
| JP8559074A JPS5515465B2 (ja) | 1973-07-26 | 1974-07-25 | |
| SE7409685A SE7409685L (ja) | 1973-07-26 | 1974-07-25 | |
| CA205,645A CA1041120A (en) | 1973-07-26 | 1974-07-25 | Process for the preparation of 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylamine |
| AT535575A AT332427B (de) | 1973-07-26 | 1975-07-11 | Verfahren zur herstellung des neuen n,n',n''- tricyclohexyl -n,n',n''- trimethyl -phosphorsaure-triamids |
| DK468976A DK140409C (da) | 1973-07-26 | 1976-10-18 | Phosphorsyretriamid til anvendelse som mellemprodukt ved fremstilling af n-cyclohexyl-n-methyl-(2-amino-3,5-dibrombenzyl)amin |
| SE7709869A SE7709869L (sv) | 1973-07-26 | 1977-09-01 | N,n'n"-tricyklohexyl-n,n'n"-trimetyl-fosforsyratriamid |
| JP664878A JPS53101344A (en) | 1973-07-26 | 1978-01-24 | Preparation of n * n*n** tricyclohexylln * n*n**trimethyll triamidephosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337931 DE2337931A1 (de) | 1973-07-26 | 1973-07-26 | Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2337931A1 true DE2337931A1 (de) | 1975-02-13 |
Family
ID=5888014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732337931 Pending DE2337931A1 (de) | 1973-07-26 | 1973-07-26 | Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS5515465B2 (ja) |
| AT (1) | AT330739B (ja) |
| BG (1) | BG24231A3 (ja) |
| CA (1) | CA1041120A (ja) |
| CH (1) | CH597147A5 (ja) |
| CS (2) | CS184839B2 (ja) |
| DE (1) | DE2337931A1 (ja) |
| DK (1) | DK135837C (ja) |
| ES (1) | ES427954A1 (ja) |
| FI (1) | FI177674A (ja) |
| HU (2) | HU168460B (ja) |
| NL (1) | NL7409046A (ja) |
| PL (1) | PL94273B1 (ja) |
| SE (2) | SE7409685L (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3107760A1 (de) * | 1981-02-28 | 1982-09-23 | Gebr. Happich Gmbh, 5600 Wuppertal | Polsterkoerper fuer den innenraum von fahrzeugen, insbesondere armlehne |
| JPH061882Y2 (ja) * | 1988-11-16 | 1994-01-19 | 株式会社東海理化電機製作所 | 車両用アウトサイドミラーのミラー本体保持構造 |
-
1973
- 1973-07-26 DE DE19732337931 patent/DE2337931A1/de active Pending
-
1974
- 1974-06-11 FI FI1776/74A patent/FI177674A/fi unknown
- 1974-06-20 AT AT510674A patent/AT330739B/de not_active IP Right Cessation
- 1974-06-25 CS CS7500001285A patent/CS184839B2/cs unknown
- 1974-06-25 CS CS4467A patent/CS170115B2/cs unknown
- 1974-06-28 BG BG7400031992A patent/BG24231A3/xx unknown
- 1974-07-04 ES ES427954A patent/ES427954A1/es not_active Expired
- 1974-07-04 NL NL7409046A patent/NL7409046A/xx not_active Application Discontinuation
- 1974-07-23 DK DK397274A patent/DK135837C/da active
- 1974-07-24 HU HUTO1000A patent/HU168460B/hu unknown
- 1974-07-24 CH CH1023574A patent/CH597147A5/xx not_active IP Right Cessation
- 1974-07-24 HU HUTO972A patent/HU167868B/hu unknown
- 1974-07-25 JP JP8559074A patent/JPS5515465B2/ja not_active Expired
- 1974-07-25 SE SE7409685A patent/SE7409685L/xx unknown
- 1974-07-25 CA CA205,645A patent/CA1041120A/en not_active Expired
- 1974-07-25 PL PL1974173005A patent/PL94273B1/pl unknown
-
1977
- 1977-09-01 SE SE7709869A patent/SE7709869L/xx unknown
-
1978
- 1978-01-24 JP JP664878A patent/JPS53101344A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL94273B1 (ja) | 1977-07-30 |
| CS170115B2 (ja) | 1976-08-27 |
| AT330739B (de) | 1976-07-12 |
| JPS53101344A (en) | 1978-09-04 |
| DK397274A (ja) | 1975-04-01 |
| ES427954A1 (es) | 1976-09-01 |
| ATA510674A (de) | 1975-10-15 |
| JPS5047945A (ja) | 1975-04-28 |
| SE7409685L (ja) | 1975-01-27 |
| SE7709869L (sv) | 1977-09-01 |
| HU168460B (ja) | 1976-04-28 |
| DK135837B (da) | 1977-07-04 |
| FI177674A (ja) | 1975-01-27 |
| NL7409046A (nl) | 1975-01-28 |
| DK135837C (da) | 1977-12-05 |
| BG24231A3 (en) | 1978-01-10 |
| JPS5515465B2 (ja) | 1980-04-23 |
| HU167868B (ja) | 1975-12-25 |
| CS184839B2 (en) | 1978-09-15 |
| CH597147A5 (ja) | 1978-03-31 |
| CA1041120A (en) | 1978-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1620694B2 (de) | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren | |
| AT504621A1 (de) | Neues verfahren zur herstellung von 4,4'-(1-methyl-1,2-ethandiyl)-bis-(2,6-piperazi dion) | |
| DE2431192C2 (de) | O,O-DiäthylS-[6-chlor-1,3-benzoxazolon-3-yl-methyl]-dithiophosphat | |
| DE2103749A1 (en) | 3-acyl-acrylic acids prepn - from a ketone and glyoxylic acid (deriv) | |
| DE2337931A1 (de) | Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin | |
| DE1670118A1 (de) | Verfahren zur Herstellung neuer Derivate des 6,11-Dihydro-dibenz[b,e]oxepins und ihrer Salze | |
| DE1912941B2 (de) | 1 -PhenyM-amino-e-methoxypridaziniumsalze | |
| CH417630A (de) | Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern | |
| DE2617967C3 (de) | Verfahren zur Herstellung von 2,4-Diamino-5-benzylpyrimidinen | |
| DE2354959A1 (de) | Neues verfahren zur herstellung von 4- amino-3,5-dihalogen-phenyl-aethanolaminen | |
| DE1695667A1 (de) | Neue Pyrrolderivate,deren Herstellung und deren Verwendung | |
| DE955591C (de) | Verfahren zur Herstellung von 2-Methyl-4-cyclohexyl-6-dimethylaminomethylphenol | |
| DE2337455A1 (de) | Neues verfahren zur herstellung von 2-amino-3,5-dibrom-benzylamin | |
| DE959097C (de) | Verfahren zur Herstellung von basisch substituierten Diarylacetonitrilen | |
| DE3320138A1 (de) | Neues nortropinderivat, verfahren zu seiner herstellung und seine verwendung | |
| DE3146373A1 (de) | 2-aminoaethanolverbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten | |
| DE2223193C3 (de) | Verfahren zur Herstellung von 2-Amino-benzylaminen | |
| DE2345443C3 (de) | Verfahren zur Herstellung von 2-Amino-benzylaminen | |
| EP1026166B1 (de) | Verfahren zur Herstellung von Folsäure | |
| AT236389B (de) | Verfahren zur Herstellung von neuen N-substituierten heterocyclischen Verbindungen | |
| DE2311637C3 (de) | Verfahren zur Herstellung von 2-Aminobenzylaminen | |
| DE2166614C3 (de) | 1 -(3-Chlorphenyl) -chinazolindion-Derlvate und Verfahren zu Ihrer Herstellung | |
| DE2130710C3 (de) | Verfahren zur Herstellung von 3'- oder 4'-Hydroxyphenyl-isonitrosomethylketonen | |
| AT214427B (de) | Verfahren zur Herstellung neuer basischer Phenoläther | |
| DE1620223A1 (de) | Verfahren zur Herstellung von Oxaphenanthridinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |