DE1643428A1 - Verfahren zur Racemisierung von Salzen des D-alpha-Amino-alpha-(3,4-dimethyloxybenzyl)-propionitrils - Google Patents
Verfahren zur Racemisierung von Salzen des D-alpha-Amino-alpha-(3,4-dimethyloxybenzyl)-propionitrilsInfo
- Publication number
- DE1643428A1 DE1643428A1 DE19671643428 DE1643428A DE1643428A1 DE 1643428 A1 DE1643428 A1 DE 1643428A1 DE 19671643428 DE19671643428 DE 19671643428 DE 1643428 A DE1643428 A DE 1643428A DE 1643428 A1 DE1643428 A1 DE 1643428A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- minutes
- amino
- salts
- propionitrile
- 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
- 150000003839 salts Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- 230000006340 racemization Effects 0.000 title claims description 11
- 239000000126 substance Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000003287 optical effect Effects 0.000 description 14
- VKDBLXQITPBAAG-UHFFFAOYSA-N propanenitrile;hydrochloride Chemical compound Cl.CCC#N VKDBLXQITPBAAG-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 2
- 125000005219 aminonitrile group Chemical group 0.000 description 2
- -1 for example Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- OFUMROLKEGKJMS-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)-3-[2-(cyclohexylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound O1COC2=C1C=CC(=C2)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CCCCC1 OFUMROLKEGKJMS-UHFFFAOYSA-N 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000965481 Darksidea alpha Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671643428 DE1643428A1 (de) | 1967-07-14 | 1967-07-14 | Verfahren zur Racemisierung von Salzen des D-alpha-Amino-alpha-(3,4-dimethyloxybenzyl)-propionitrils |
| GB3279668A GB1163858A (en) | 1967-07-14 | 1968-07-10 | Process for the Racemization of Salts of D-alpha-Amino-alpha-(3,4-Dimethoxybenzyl)-Propionitrile |
| CH1047568A CH495962A (de) | 1967-07-14 | 1968-07-12 | Verfahren zur Racemisierung von Salzen des D-a-Amino-a-(3,4-dimethoxybenzyl)-propionitrils |
| BE718049D BE718049A (cs) | 1967-07-14 | 1968-07-12 | |
| NL6809905A NL6809905A (cs) | 1967-07-14 | 1968-07-12 | |
| FR1576682D FR1576682A (cs) | 1967-07-14 | 1968-07-15 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671643428 DE1643428A1 (de) | 1967-07-14 | 1967-07-14 | Verfahren zur Racemisierung von Salzen des D-alpha-Amino-alpha-(3,4-dimethyloxybenzyl)-propionitrils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643428A1 true DE1643428A1 (de) | 1971-05-27 |
Family
ID=5684311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643428 Pending DE1643428A1 (de) | 1967-07-14 | 1967-07-14 | Verfahren zur Racemisierung von Salzen des D-alpha-Amino-alpha-(3,4-dimethyloxybenzyl)-propionitrils |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE718049A (cs) |
| CH (1) | CH495962A (cs) |
| DE (1) | DE1643428A1 (cs) |
| FR (1) | FR1576682A (cs) |
| GB (1) | GB1163858A (cs) |
| NL (1) | NL6809905A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0683145A1 (en) * | 1990-09-20 | 1995-11-22 | E.I. Du Pont De Nemours And Company | A method for racemizing nitriles |
-
1967
- 1967-07-14 DE DE19671643428 patent/DE1643428A1/de active Pending
-
1968
- 1968-07-10 GB GB3279668A patent/GB1163858A/en not_active Expired
- 1968-07-12 CH CH1047568A patent/CH495962A/de not_active IP Right Cessation
- 1968-07-12 NL NL6809905A patent/NL6809905A/xx unknown
- 1968-07-12 BE BE718049D patent/BE718049A/xx unknown
- 1968-07-15 FR FR1576682D patent/FR1576682A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0683145A1 (en) * | 1990-09-20 | 1995-11-22 | E.I. Du Pont De Nemours And Company | A method for racemizing nitriles |
Also Published As
| Publication number | Publication date |
|---|---|
| BE718049A (cs) | 1969-01-13 |
| CH495962A (de) | 1970-09-15 |
| GB1163858A (en) | 1969-09-10 |
| FR1576682A (cs) | 1969-08-01 |
| NL6809905A (cs) | 1969-01-16 |
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