DE611501C - Verfahren zur Herstellung von Abkoemmlingen des optisch aktiven oder racemischen 1-Phenyl-2-methylaminopropan-1-ols - Google Patents
Verfahren zur Herstellung von Abkoemmlingen des optisch aktiven oder racemischen 1-Phenyl-2-methylaminopropan-1-olsInfo
- Publication number
- DE611501C DE611501C DEC47407D DEC0047407D DE611501C DE 611501 C DE611501 C DE 611501C DE C47407 D DEC47407 D DE C47407D DE C0047407 D DEC0047407 D DE C0047407D DE 611501 C DE611501 C DE 611501C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- methylaminopropan
- racemic
- optically active
- preparation
- 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 claims description 4
- KWGRBVOPPLSCSI-UHFFFAOYSA-N 2-(methylamino)-1-phenylpropan-1-ol Chemical compound CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KWGRBVOPPLSCSI-HNHGDDPOSA-N (2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-HNHGDDPOSA-N 0.000 description 1
- WUBNORHFBNRWRF-UHFFFAOYSA-N 1-(benzylamino)propan-1-ol Chemical compound CCC(O)NCC1=CC=CC=C1 WUBNORHFBNRWRF-UHFFFAOYSA-N 0.000 description 1
- SJUPSBNWNDADBN-UHFFFAOYSA-N 1-(benzylamino)propan-1-ol hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CNC(CC)O SJUPSBNWNDADBN-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- -1 toluenesulfonic acid ester Chemical class 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
- C07C215/22—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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC47407D DE611501C (de) | 1933-01-13 | 1933-01-13 | Verfahren zur Herstellung von Abkoemmlingen des optisch aktiven oder racemischen 1-Phenyl-2-methylaminopropan-1-ols |
| NL68098A NL36662C (enrdf_load_stackoverflow) | 1933-01-13 | 1934-01-12 | |
| BE400851A BE400851A (enrdf_load_stackoverflow) | 1933-01-13 | 1934-01-12 | |
| BE416814A BE416814R (enrdf_load_stackoverflow) | 1933-01-13 | 1936-08-01 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC47407D DE611501C (de) | 1933-01-13 | 1933-01-13 | Verfahren zur Herstellung von Abkoemmlingen des optisch aktiven oder racemischen 1-Phenyl-2-methylaminopropan-1-ols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE611501C true DE611501C (de) | 1935-03-30 |
Family
ID=7026553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC47407D Expired DE611501C (de) | 1933-01-13 | 1933-01-13 | Verfahren zur Herstellung von Abkoemmlingen des optisch aktiven oder racemischen 1-Phenyl-2-methylaminopropan-1-ols |
Country Status (3)
| Country | Link |
|---|---|
| BE (2) | BE400851A (enrdf_load_stackoverflow) |
| DE (1) | DE611501C (enrdf_load_stackoverflow) |
| NL (1) | NL36662C (enrdf_load_stackoverflow) |
-
1933
- 1933-01-13 DE DEC47407D patent/DE611501C/de not_active Expired
-
1934
- 1934-01-12 NL NL68098A patent/NL36662C/nl active
- 1934-01-12 BE BE400851A patent/BE400851A/fr unknown
-
1936
- 1936-08-01 BE BE416814A patent/BE416814R/fr active
Also Published As
| Publication number | Publication date |
|---|---|
| NL36662C (enrdf_load_stackoverflow) | 1935-05-15 |
| BE416814R (enrdf_load_stackoverflow) | 1936-09-30 |
| BE400851A (enrdf_load_stackoverflow) | 1934-03-31 |
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