FI67076C - Foerfarande foer framstaellning av 2-dietylamino-1-metyletylsestrar av substituerade hydroxicykloheksankarboxylsyror - Google Patents
Foerfarande foer framstaellning av 2-dietylamino-1-metyletylsestrar av substituerade hydroxicykloheksankarboxylsyror Download PDFInfo
- Publication number
- FI67076C FI67076C FI793636A FI793636A FI67076C FI 67076 C FI67076 C FI 67076C FI 793636 A FI793636 A FI 793636A FI 793636 A FI793636 A FI 793636A FI 67076 C FI67076 C FI 67076C
- Authority
- FI
- Finland
- Prior art keywords
- diethylamino
- mixture
- formula
- temperature
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- BPOVRAAUERBWFK-UHFFFAOYSA-N 1-hydroxycyclohexane-1-carboxylic acid Chemical class OC(=O)C1(O)CCCCC1 BPOVRAAUERBWFK-UHFFFAOYSA-N 0.000 claims description 11
- -1 2-diethylamino-1-methylethyl esters Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- WNKXRJOYUCAQLE-UHFFFAOYSA-N 2-chloro-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CC(C)Cl WNKXRJOYUCAQLE-UHFFFAOYSA-N 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 239000011874 heated mixture Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
- QOHJWGXVMZSTAZ-UHFFFAOYSA-N 2-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CC(C)Cl QOHJWGXVMZSTAZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VCZPUGSOJXZKIP-YPMHNXCESA-N (1S,2R)-cicloxilic acid Chemical compound OC(=O)[C@H]1CCCC[C@]1(O)C1=CC=CC=C1 VCZPUGSOJXZKIP-YPMHNXCESA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000404883 Pisa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000001663 anti-spastic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/12—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3016378 | 1978-11-24 | ||
| IT30163/78A IT1100581B (it) | 1978-11-24 | 1978-11-24 | Procedimento per la fabbricazione di esteri easici di acidi idrossicicicloesancarbossilici sostituti |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI793636A FI793636A (fi) | 1980-05-25 |
| FI67076B FI67076B (fi) | 1984-09-28 |
| FI67076C true FI67076C (fi) | 1985-01-10 |
Family
ID=11229242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI793636A FI67076C (fi) | 1978-11-24 | 1979-11-20 | Foerfarande foer framstaellning av 2-dietylamino-1-metyletylsestrar av substituerade hydroxicykloheksankarboxylsyror |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4336398A (nl) |
| JP (1) | JPS5594343A (nl) |
| AR (1) | AR221386A1 (nl) |
| AT (1) | AT369355B (nl) |
| AU (1) | AU527502B2 (nl) |
| BE (1) | BE880189A (nl) |
| CA (1) | CA1146174A (nl) |
| CH (1) | CH642940A5 (nl) |
| DE (1) | DE2947160A1 (nl) |
| DK (1) | DK154830C (nl) |
| ES (1) | ES485956A1 (nl) |
| FI (1) | FI67076C (nl) |
| FR (1) | FR2442225A1 (nl) |
| GB (1) | GB2038813B (nl) |
| GR (1) | GR73996B (nl) |
| IL (1) | IL58711A (nl) |
| IN (1) | IN151854B (nl) |
| IT (1) | IT1100581B (nl) |
| MX (1) | MX6243E (nl) |
| NL (1) | NL188799C (nl) |
| NO (1) | NO147522C (nl) |
| PH (1) | PH15969A (nl) |
| PT (1) | PT70461A (nl) |
| SE (1) | SE437372B (nl) |
| ZA (1) | ZA796192B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5668655A (en) * | 1979-11-08 | 1981-06-09 | Mitsui Toatsu Chem Inc | Allyl carbamic acid ester derivative |
| IT1190755B (it) * | 1982-04-01 | 1988-02-24 | Guidotti Internationale Sa Hol | Procedimento per la preparazione di derivati di 2-dietilamino-1-metiletil cis-1-idrossi-(bicicloesil)-2-carbossilato |
| CN106631760B (zh) * | 2015-10-29 | 2019-05-28 | 上海医药工业研究院 | 顺-1-羟基-[1,1’-双(环己烷)]-2-羧酸的制备工艺 |
| CN108069846B (zh) * | 2016-11-17 | 2020-11-03 | 上海医药工业研究院 | 顺-1-羟基-[1,1′-双(环己基)]-2-甲酸的拆分方法及中间体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA539593A (en) * | 1957-04-16 | L. Beman Floyd | Dialkylaminoalkyl esters of phenyl substituted dihydroxybenzoic acids | |
| CH522592A (de) * | 1966-04-29 | 1972-06-30 | Guidotti & C Spa Labor | Verfahren zur Herstellung von therapeutisch wirksamen Hydroxycyclohexancarbonsäureestern |
| US3700675A (en) * | 1970-09-11 | 1972-10-24 | Luigi Turbanti | Ester of 2-hydroxy-cyclohexane-2-substituted carboxylic acids |
-
1978
- 1978-11-24 IT IT30163/78A patent/IT1100581B/it active
-
1979
- 1979-11-13 IL IL58711A patent/IL58711A/xx not_active IP Right Cessation
- 1979-11-14 ES ES485956A patent/ES485956A1/es not_active Expired
- 1979-11-16 PT PT70461A patent/PT70461A/pt unknown
- 1979-11-16 ZA ZA00796192A patent/ZA796192B/xx unknown
- 1979-11-16 FR FR7928287A patent/FR2442225A1/fr active Granted
- 1979-11-16 GR GR60522A patent/GR73996B/el unknown
- 1979-11-20 FI FI793636A patent/FI67076C/fi not_active IP Right Cessation
- 1979-11-20 AT AT0739979A patent/AT369355B/de not_active IP Right Cessation
- 1979-11-20 SE SE7909596A patent/SE437372B/sv not_active IP Right Cessation
- 1979-11-21 BE BE0/198229A patent/BE880189A/fr not_active IP Right Cessation
- 1979-11-21 JP JP15012479A patent/JPS5594343A/ja active Granted
- 1979-11-22 NO NO793790A patent/NO147522C/no unknown
- 1979-11-22 DE DE19792947160 patent/DE2947160A1/de active Granted
- 1979-11-22 PH PH23316A patent/PH15969A/en unknown
- 1979-11-22 NL NLAANVRAGE7908529,A patent/NL188799C/nl not_active IP Right Cessation
- 1979-11-23 MX MX798497U patent/MX6243E/es unknown
- 1979-11-23 AU AU53129/79A patent/AU527502B2/en not_active Ceased
- 1979-11-23 AR AR279010D patent/AR221386A1/es active
- 1979-11-23 CA CA000340561A patent/CA1146174A/en not_active Expired
- 1979-11-23 GB GB7940662A patent/GB2038813B/en not_active Expired
- 1979-11-23 US US06/096,938 patent/US4336398A/en not_active Expired - Lifetime
- 1979-11-23 DK DK498279A patent/DK154830C/da not_active IP Right Cessation
- 1979-11-23 CH CH1043979A patent/CH642940A5/it not_active IP Right Cessation
- 1979-11-25 IN IN1229/CAL/79A patent/IN151854B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: LABORATORIO GUIDOTTI E C. S.P.A. |