CH418353A - Verfahren zur Herstellung von 1-Phenyl-1-(o-chlorphenyl)-3-tert.-aminopropanolen-(1) - Google Patents
Verfahren zur Herstellung von 1-Phenyl-1-(o-chlorphenyl)-3-tert.-aminopropanolen-(1)Info
- Publication number
- CH418353A CH418353A CH1676364A CH1676364A CH418353A CH 418353 A CH418353 A CH 418353A CH 1676364 A CH1676364 A CH 1676364A CH 1676364 A CH1676364 A CH 1676364A CH 418353 A CH418353 A CH 418353A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- chlorophenyl
- ether
- ccm
- aminopropanol
- Prior art date
Links
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- -1 N-methylpiperazino Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 claims description 2
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical group CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 239000007832 Na2SO4 Substances 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0025420 | 1958-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH418353A true CH418353A (de) | 1966-08-15 |
Family
ID=7091623
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1676364A CH418353A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlorphenyl)-3-tert.-aminopropanolen-(1) |
| CH7080859A CH408053A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(chlor-phenyl)-3-tert.-aminopropanolen-(1) |
| CH745764A CH441377A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlor-phenyl)-3-tert.-aminopropanolen-(1) |
| CH745864A CH439327A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlor-phenyl)-3-tert.-amino-propanolen-(1) |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7080859A CH408053A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(chlor-phenyl)-3-tert.-aminopropanolen-(1) |
| CH745764A CH441377A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlor-phenyl)-3-tert.-aminopropanolen-(1) |
| CH745864A CH439327A (de) | 1958-04-05 | 1959-03-16 | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlor-phenyl)-3-tert.-amino-propanolen-(1) |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE577370A (OSRAM) |
| CH (4) | CH418353A (OSRAM) |
| FR (1) | FR451M (OSRAM) |
-
1959
- 1959-03-16 CH CH1676364A patent/CH418353A/de unknown
- 1959-03-16 CH CH7080859A patent/CH408053A/de unknown
- 1959-03-16 CH CH745764A patent/CH441377A/de unknown
- 1959-03-16 CH CH745864A patent/CH439327A/de unknown
- 1959-04-04 BE BE577370A patent/BE577370A/fr unknown
-
1960
- 1960-08-30 FR FR837161A patent/FR451M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CH439327A (de) | 1967-07-15 |
| BE577370A (fr) | 1959-07-31 |
| CH408053A (de) | 1966-02-28 |
| FR451M (OSRAM) | 1961-04-24 |
| CH441377A (de) | 1967-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE842203C (de) | Verfahren zur Herstellung von neuen Piperazinderivaten | |
| CH418353A (de) | Verfahren zur Herstellung von 1-Phenyl-1-(o-chlorphenyl)-3-tert.-aminopropanolen-(1) | |
| DE2114884A1 (de) | Basisch substituierte Derivate des 1(2H)-Phthalazinons | |
| AT211299B (de) | Verfahren zur Herstellung von 1-Phenyl-1(o-chlorphenyl)-3-tert.aminopropanolen-(1) | |
| US2881172A (en) | Chemical compounds | |
| DE935127C (de) | Verfahren zur Herstellung von N-Aryl-N'-aminoalkylharnstoffen | |
| AT229873B (de) | Verfahren zur Herstellung 1, 4-disubstituierter Piperazinderivate | |
| AT235825B (de) | Verfahren zur Herstellung neuer α, α-Diphenyl-α-propinoxyessigsäurederivate und ihrer Salze | |
| AT270654B (de) | Verfahren zur Herstellung von neuen Piperazin-Derivaten und deren Salzen | |
| AT211300B (de) | Verfahren zur Herstellung von neuen 1-Phenyl-1-(o-chlorphenyl)-3-tert.aminopropanolen-(1) | |
| DE950550C (de) | Verfahren zur Herstellung von basisch substituierten Phenylcycloalkenylpropanolen | |
| AT273142B (de) | Verfahren zur Herstellung von neuen Piperazin-Derivaten und deren Salzen | |
| AT203497B (de) | Verfahren zur Herstellung von neuen Diphenylmethan-derivaten, ihren Säuresalzen und quartären Salzen | |
| AT205031B (de) | Verfahren zur Herstellung von neuen, basisch substituierten Derivaten von 4-Aza-phenthiazinen bzw. ihren Salzen | |
| AT220144B (de) | Verfahren zur Herstellung von neuen tertiären Aminen, sowie deren Säureadditions- und quaternären Ammoniumsalzen | |
| AT238159B (de) | Verfahren zur Herstellung von neuen Dihalogen-amino-benzylaminen und deren Säureadditionssalzen mit anorganischen oder organischen Säuren | |
| AT252220B (de) | Verfahren zur Herstellung von neuen Aminoketonen und ihren Salzen | |
| AT333253B (de) | Verfahren zur herstellung von neuen racemischen und optischen aktiven aminophenyl-athanolaminen | |
| AT217045B (de) | Verfahren zur Herstellung von neuen monoalkylierten bzw. monohalogenierten N-Derivaten von 10,11-Dihydro-5H-dibenzo[b,f]azepinen und 5H-Dibenzo[b,f]azepinen | |
| AT254204B (de) | Verfahren zur Herstellung von neuen Aminen | |
| AT238180B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| AT242137B (de) | Verfahren zur Herstellung von neuen Derivaten des 4-Aminobutin-(2, 3)-ols-1 und deren Salzen | |
| AT254850B (de) | Verfahren zur Herstellung neuer sekundärer Amine und ihrer Salze | |
| AT228206B (de) | Verfahren zur Herstellung von neuen N-Phenylpiperazinderivaten | |
| AT238186B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen |