DE2602846C2 - Verfahren zur Herstellung von 2-(2-Thienyl)äthylaminen - Google Patents
Verfahren zur Herstellung von 2-(2-Thienyl)äthylaminenInfo
- Publication number
- DE2602846C2 DE2602846C2 DE19762602846 DE2602846A DE2602846C2 DE 2602846 C2 DE2602846 C2 DE 2602846C2 DE 19762602846 DE19762602846 DE 19762602846 DE 2602846 A DE2602846 A DE 2602846A DE 2602846 C2 DE2602846 C2 DE 2602846C2
- Authority
- DE
- Germany
- Prior art keywords
- thienyl
- ethylamines
- preparation
- phthalimide
- general formula
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical class NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 title description 8
- -1 2-thienyl - Chemical class 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IFXJWKYMTDETOP-UHFFFAOYSA-N 2-(2-thiophen-2-ylethyl)isoindole-1,3-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1CCC1=CC=CS1 IFXJWKYMTDETOP-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000005891 transamination reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT7949199A IT7949199A0 (it) | 1975-01-31 | 1979-05-28 | Procedimento per preparare(tienil-2)-2-etilammina e suoi derivati |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7503142A FR2299332A1 (fr) | 1975-01-31 | 1975-01-31 | Procede de preparation de la (thienyl-2)-2-ethylamine et de ses derives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2602846A1 DE2602846A1 (de) | 1976-08-05 |
| DE2602846C2 true DE2602846C2 (de) | 1986-02-13 |
Family
ID=9150600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762602846 Expired DE2602846C2 (de) | 1975-01-31 | 1976-01-27 | Verfahren zur Herstellung von 2-(2-Thienyl)äthylaminen |
Country Status (8)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415671A1 (fr) * | 1978-01-25 | 1979-08-24 | Parcor | Procede de preparation d'amino-2 ethyl-2 thiophene par voie electrochimique |
| ZA881227B (en) * | 1987-02-26 | 1988-10-26 | Merrell Pharma Inc | Heterocyclyl-2-propyn-1-amines |
| DK0439404T3 (da) * | 1990-01-25 | 1996-02-12 | Sanofi Sa | Fremstilling af 2-(2-thienyl)-alkylaminer og derivater deraf samt synthese af 4,5,6,7-thieno- (3,2-c)pyridinderivater ud fra disse |
| DE10248479A1 (de) * | 2002-10-17 | 2004-05-06 | Consortium für elektrochemische Industrie GmbH | Verfahren zur Herstellung von Thienyl-substituierten sekundären Aminoalkoholen |
| DE10248480A1 (de) * | 2002-10-17 | 2004-05-06 | Consortium für elektrochemische Industrie GmbH | Verfahren zur Herstellung von Thienyl-substituierten sekundären Aminoalkoholen |
-
1975
- 1975-01-31 FR FR7503142A patent/FR2299332A1/fr active Granted
- 1975-12-12 CH CH1613775A patent/CH613700A5/xx not_active IP Right Cessation
-
1976
- 1976-01-02 ES ES444036A patent/ES444036A1/es not_active Expired
- 1976-01-09 JP JP239376A patent/JPS51118760A/ja active Granted
- 1976-01-14 BE BE163500A patent/BE837552A/xx not_active IP Right Cessation
- 1976-01-27 DE DE19762602846 patent/DE2602846C2/de not_active Expired
- 1976-01-30 CA CA245,047A patent/CA1055509A/en not_active Expired
- 1976-01-30 GB GB384976A patent/GB1469226A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2299332A1 (fr) | 1976-08-27 |
| ES444036A1 (es) | 1977-04-16 |
| JPS51118760A (en) | 1976-10-18 |
| BE837552A (fr) | 1976-07-14 |
| CA1055509A (en) | 1979-05-29 |
| DE2602846A1 (de) | 1976-08-05 |
| JPS6225666B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-04 |
| FR2299332B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-23 |
| GB1469226A (en) | 1977-04-06 |
| CH613700A5 (en) | 1979-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SANOFI, PARIS, FR |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: VON KREISLER, A., DIPL.-CHEM. SELTING, G., DIPL.-ING. WERNER, H., DIPL.-CHEM. DR.RER.NAT. SCHOENWALD, K., DR.-ING. FUES, J., DIPL.-CHEM. DR.RER.NAT. BOECKMANN GEN. DALLMEYER, G., DIPL.-ING., PAT.-ANWAELTE, 5000 KOELN |