CA1068289A - Process for the preparation of 2-aminoindane derivatives - Google Patents
Process for the preparation of 2-aminoindane derivativesInfo
- Publication number
- CA1068289A CA1068289A CA267,951A CA267951A CA1068289A CA 1068289 A CA1068289 A CA 1068289A CA 267951 A CA267951 A CA 267951A CA 1068289 A CA1068289 A CA 1068289A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- aminoindane
- phenyl
- hydrochloride
- iii
- 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
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical class C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 54
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001412 amines Chemical class 0.000 claims abstract description 26
- MHVHCDLCLNXADJ-UHFFFAOYSA-N n-phenyl-2,3-dihydro-1h-inden-2-amine Chemical compound C1C2=CC=CC=C2CC1NC1=CC=CC=C1 MHVHCDLCLNXADJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229910018954 NaNH2 Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 239000012458 free base Substances 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 159000000000 sodium salts Chemical class 0.000 abstract description 4
- -1 benzene or toluene Chemical compound 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- MHWBCRLIAXHKIB-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1h-inden-2-amine Chemical compound NC1CC2=CC=CC=C2C1C1=CC=CC=C1 MHWBCRLIAXHKIB-UHFFFAOYSA-N 0.000 description 2
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 241000375392 Tana Species 0.000 description 1
- 240000004543 Vicia ervilia Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940095054 ammoniac Drugs 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- NZLBHDRPUJLHCE-UHFFFAOYSA-N aprindine Chemical compound C1C2=CC=CC=C2CC1N(CCCN(CC)CC)C1=CC=CC=C1 NZLBHDRPUJLHCE-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU74197A LU74197A1 (en:Method) | 1976-01-16 | 1976-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068289A true CA1068289A (en) | 1979-12-18 |
Family
ID=19728141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,951A Expired CA1068289A (en) | 1976-01-16 | 1976-12-15 | Process for the preparation of 2-aminoindane derivatives |
Country Status (21)
| Country | Link |
|---|---|
| AR (1) | AR211042A1 (en:Method) |
| AT (1) | AT347444B (en:Method) |
| AU (1) | AU503658B2 (en:Method) |
| CA (1) | CA1068289A (en:Method) |
| CH (1) | CH617663A5 (en:Method) |
| CS (1) | CS193538B2 (en:Method) |
| DD (1) | DD123598A5 (en:Method) |
| DK (1) | DK4677A (en:Method) |
| ES (1) | ES454939A1 (en:Method) |
| FI (1) | FI770039A7 (en:Method) |
| HU (1) | HU174694B (en:Method) |
| IL (1) | IL51125A (en:Method) |
| LU (1) | LU74197A1 (en:Method) |
| MX (1) | MX4651E (en:Method) |
| NO (1) | NO143217C (en:Method) |
| NZ (1) | NZ182904A (en:Method) |
| PL (1) | PL104367B1 (en:Method) |
| PT (1) | PT66020B (en:Method) |
| SE (1) | SE7700321L (en:Method) |
| SU (1) | SU640658A3 (en:Method) |
| ZA (1) | ZA767468B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7592458B2 (en) | 2006-07-21 | 2009-09-22 | Wright George E | Dermal anesthetic compounds and pharmaceutical compositions for inducing local anesthesia and mitigating neuropathic pain |
| US7718674B2 (en) | 2004-09-27 | 2010-05-18 | Bridge Pharma, Inc. | Methods of relieving neuropathic pain with the S-isomer of 2-{2[N-(2-indanyl)-N-phenylamino]ethyl}piperidine |
-
1976
- 1976-01-16 LU LU74197A patent/LU74197A1/xx unknown
- 1976-03-01 DD DD191667A patent/DD123598A5/xx unknown
- 1976-03-04 HU HU76CI1646A patent/HU174694B/hu unknown
- 1976-03-11 CS CS761606A patent/CS193538B2/cs unknown
- 1976-03-12 PL PL1976187911A patent/PL104367B1/pl unknown
- 1976-03-16 SU SU762333209A patent/SU640658A3/ru active
- 1976-12-15 CA CA267,951A patent/CA1068289A/en not_active Expired
- 1976-12-15 ZA ZA767468A patent/ZA767468B/xx unknown
- 1976-12-16 NZ NZ182904A patent/NZ182904A/xx unknown
- 1976-12-17 IL IL51125A patent/IL51125A/xx unknown
- 1976-12-17 AU AU20677/76A patent/AU503658B2/en not_active Expired
- 1976-12-27 AT AT966976A patent/AT347444B/de not_active IP Right Cessation
- 1976-12-28 PT PT66020A patent/PT66020B/pt unknown
-
1977
- 1977-01-05 AR AR266112A patent/AR211042A1/es active
- 1977-01-05 MX MX775301U patent/MX4651E/es unknown
- 1977-01-06 DK DK4677A patent/DK4677A/da unknown
- 1977-01-06 FI FI770039A patent/FI770039A7/fi not_active Application Discontinuation
- 1977-01-11 ES ES454939A patent/ES454939A1/es not_active Expired
- 1977-01-13 SE SE7700321A patent/SE7700321L/xx unknown
- 1977-01-14 NO NO770126A patent/NO143217C/no unknown
- 1977-01-14 CH CH49977A patent/CH617663A5/fr not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7718674B2 (en) | 2004-09-27 | 2010-05-18 | Bridge Pharma, Inc. | Methods of relieving neuropathic pain with the S-isomer of 2-{2[N-(2-indanyl)-N-phenylamino]ethyl}piperidine |
| US7592458B2 (en) | 2006-07-21 | 2009-09-22 | Wright George E | Dermal anesthetic compounds and pharmaceutical compositions for inducing local anesthesia and mitigating neuropathic pain |
Also Published As
| Publication number | Publication date |
|---|---|
| PT66020A (en) | 1977-01-01 |
| AT347444B (de) | 1978-12-27 |
| AU503658B2 (en) | 1979-09-13 |
| IL51125A (en) | 1980-06-30 |
| LU74197A1 (en:Method) | 1977-07-22 |
| PL104367B1 (pl) | 1979-08-31 |
| NO143217C (no) | 1981-01-07 |
| DD123598A5 (en:Method) | 1977-01-05 |
| HU174694B (hu) | 1980-03-28 |
| NO770126L (no) | 1977-07-19 |
| ATA966976A (de) | 1978-05-15 |
| MX4651E (es) | 1982-07-16 |
| ES454939A1 (es) | 1977-12-01 |
| IL51125A0 (en) | 1977-02-28 |
| DK4677A (da) | 1977-07-17 |
| CH617663A5 (en) | 1980-06-13 |
| NO143217B (no) | 1980-09-22 |
| ZA767468B (en) | 1977-11-30 |
| SU640658A3 (ru) | 1978-12-30 |
| AR211042A1 (es) | 1977-10-14 |
| NZ182904A (en) | 1979-01-11 |
| AU2067776A (en) | 1978-06-22 |
| PT66020B (en) | 1978-06-19 |
| CS193538B2 (en) | 1979-10-31 |
| FI770039A7 (en:Method) | 1977-07-17 |
| SE7700321L (sv) | 1977-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0081234B1 (en) | Novel method of preparing benzothiazepine derivatives | |
| CA1068289A (en) | Process for the preparation of 2-aminoindane derivatives | |
| EP0068407A1 (en) | Aminosulfonylbenzoic acid derivatives | |
| CA2158763C (en) | Novel process for preparation of clonidine derivatives | |
| US5155226A (en) | Method for the preparation of 9-amino-1,2,3,4-tetrahydroacridine | |
| CA1170660A (en) | Bis-tetrazolemethyl thiols | |
| Catsoulacos et al. | Thiazo compounds. Derivatives of 4, 5-dihydro-7, 8-dimethoxybenzothiazepin-3-one 1, 1-dioxides | |
| CA1072093A (en) | Process for the production of basic triphenylalkene derivatives | |
| JP2678758B2 (ja) | 新規なプロパン誘導体 | |
| CA1130305A (en) | Process for the preparation of n,n'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
| US5106846A (en) | 2,3-thiomorpholinedione-2-oxime derivatives and pharmaceutical compositions containing them | |
| GB1589882A (en) | Tetrazole-5-thiols | |
| Krapcho et al. | Synthesis and rearrangements of dihydro-1, 4-oxazepine and dihydro-1, 4-thiazepine derivatives | |
| EP0131472A2 (en) | 5-Mercapto-1,2,3-thiadiazoles composition and process for preparing the same | |
| CA1119179A (en) | Process for preparing n-tritylimidazole compounds | |
| US4189444A (en) | Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
| Kleschick et al. | Regiospecific synthesis of arenesulfonamide derivatives of 3, 5-diamino-1, 2, 4-triazole | |
| US4355169A (en) | Thiazolidinyl-substituted phenyl sulfonamides | |
| US4656286A (en) | Aminoethanethiol and thiazolidine compounds | |
| US3864330A (en) | Benzodiazepine derivatives and production thereof | |
| CA1224477A (en) | Process for preparing dialkyl propanediimidate dihydrohalides | |
| RU1436454C (ru) | Способ получени 2-(алкоксифенил)этиламинов | |
| US3697537A (en) | 2-(aryloxy)-2-thiazolinium compounds | |
| SU596583A1 (ru) | Способ получени 2-замещенных-4-оксо6-ацилокси-1,3,4-тиазинов | |
| CA1308732C (en) | Preparation of amine derivatives |