DE169819C - - Google Patents
Info
- Publication number
- DE169819C DE169819C DENDAT169819D DE169819DA DE169819C DE 169819 C DE169819 C DE 169819C DE NDAT169819 D DENDAT169819 D DE NDAT169819D DE 169819D A DE169819D A DE 169819DA DE 169819 C DE169819 C DE 169819C
- Authority
- DE
- Germany
- Prior art keywords
- boils
- hydrochloride
- pressure
- under
- alcohol
- 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.)
- Active
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229910014033 C-OH Inorganic materials 0.000 claims description 5
- 229910014570 C—OH Inorganic materials 0.000 claims description 5
- -1 Dimethylaminodimethylbenzyl carbinol Chemical compound 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- BCDGQXUMWHRQCB-UHFFFAOYSA-N 1-Amino-2-propanone Chemical class CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- GDXMMBDEMOUTNS-UHFFFAOYSA-N 1-(diethylamino)propan-2-one Chemical compound CCN(CC)CC(C)=O GDXMMBDEMOUTNS-UHFFFAOYSA-N 0.000 claims 1
- UGXRYVLOOJYDNW-UHFFFAOYSA-N C(C)N(CC)OC(C1=CC=CC=C1)(C)C Chemical compound C(C)N(CC)OC(C1=CC=CC=C1)(C)C UGXRYVLOOJYDNW-UHFFFAOYSA-N 0.000 claims 1
- JKGCTGHQGHTSSJ-UHFFFAOYSA-N CN(C)OC(CCC(C)C)(C)C Chemical compound CN(C)OC(CCC(C)C)(C)C JKGCTGHQGHTSSJ-UHFFFAOYSA-N 0.000 claims 1
- AAPDFQUOUHITNA-UHFFFAOYSA-N CN(C)OC(CCC)(C)C Chemical compound CN(C)OC(CCC)(C)C AAPDFQUOUHITNA-UHFFFAOYSA-N 0.000 claims 1
- JUUNYTVCJDPKMB-UHFFFAOYSA-M [Br-].CC(C)CC[Mg+] Chemical compound [Br-].CC(C)CC[Mg+] JUUNYTVCJDPKMB-UHFFFAOYSA-M 0.000 claims 1
- YQMARKZVVTYGOK-UHFFFAOYSA-M [Br-].CCC[Mg+] Chemical compound [Br-].CCC[Mg+] YQMARKZVVTYGOK-UHFFFAOYSA-M 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 claims 1
- 150000003944 halohydrins Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 2
- AUPXBVDHVRZMIB-UHFFFAOYSA-M C[Mg]I Chemical compound C[Mg]I AUPXBVDHVRZMIB-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
- QQXLDOJGLXJCSE-KNVOCYPGSA-N Tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 2
- 125000001650 tertiary alcohol group Chemical group 0.000 description 2
- VMCSODPPPQQBSY-UHFFFAOYSA-N 3-[(dimethylamino)methyl]pentan-3-ol Chemical compound CCC(O)(CC)CN(C)C VMCSODPPPQQBSY-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- RDSSCARDOFBKMY-UHFFFAOYSA-N CN(C)OC(C1=CC=CC=C1)(C)C Chemical compound CN(C)OC(C1=CC=CC=C1)(C)C RDSSCARDOFBKMY-UHFFFAOYSA-N 0.000 description 1
- PWFOLWIQYPIAGA-UHFFFAOYSA-N N-methyl-N-[(2-methylpropan-2-yl)oxy]methanamine Chemical compound CN(C)OC(C)(C)C PWFOLWIQYPIAGA-UHFFFAOYSA-N 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical compound O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M Phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L Platinum(II) chloride Chemical class Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetone amine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000003444 anaesthetic Effects 0.000 description 1
- 230000000202 analgesic Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- ZPUCINDJVBIVPJ-BARDWOONSA-N cocaine Natural products O([C@@H]1C[C@H]2CC[C@H](N2C)[C@@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-BARDWOONSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- LRZFEBJUJIQVDQ-UHFFFAOYSA-N methyl 2-(dimethylamino)acetate Chemical compound COC(=O)CN(C)C LRZFEBJUJIQVDQ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 230000000699 topical Effects 0.000 description 1
- ZYHGIAPHLSTGMX-UHFFFAOYSA-N β-Eucaine Chemical compound C1C(C)(C)NC(C)CC1OC(=O)C1=CC=CC=C1 ZYHGIAPHLSTGMX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE169819C true DE169819C (xx) |
Family
ID=434907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT169819D Active DE169819C (xx) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE169819C (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2517695A (en) * | 1945-07-13 | 1950-08-08 | Ciba Pharm Prod Inc | Production of 1-alkyl 4-phenylpiperidyl 4-ketones |
| WO2010010412A2 (en) * | 2008-07-25 | 2010-01-28 | LUKÁCS, Gyula | Method for the preparation of n-methyl-aryloxy-propanamine derivatives |
-
0
- DE DENDAT169819D patent/DE169819C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2517695A (en) * | 1945-07-13 | 1950-08-08 | Ciba Pharm Prod Inc | Production of 1-alkyl 4-phenylpiperidyl 4-ketones |
| WO2010010412A2 (en) * | 2008-07-25 | 2010-01-28 | LUKÁCS, Gyula | Method for the preparation of n-methyl-aryloxy-propanamine derivatives |
| WO2010010412A3 (en) * | 2008-07-25 | 2010-05-27 | Egis Gyogyszergyar Nilvanosan | Method for the preparation of n-methyl-aryloxy-propanamine derivatives |
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