NO115758B - - Google Patents
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- Publication number
- NO115758B NO115758B NO16394666A NO16394666A NO115758B NO 115758 B NO115758 B NO 115758B NO 16394666 A NO16394666 A NO 16394666A NO 16394666 A NO16394666 A NO 16394666A NO 115758 B NO115758 B NO 115758B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- piperidyl
- phenyl
- racemate
- antipodes
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- -1 methylenedioxy group Chemical group 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- GPOGKMPXBDGPJH-UHFFFAOYSA-N butan-2-yl acetate hydrochloride Chemical compound Cl.CCC(C)OC(C)=O GPOGKMPXBDGPJH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B7/00—Special arrangements or measures in connection with doors or windows
- E06B7/28—Other arrangements on doors or windows, e.g. door-plates, windows adapted to carry plants, hooks for window cleaners
- E06B7/30—Peep-holes; Devices for speaking through; Doors having windows
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B5/00—Doors, windows, or like closures for special purposes; Border constructions therefor
- E06B5/10—Doors, windows, or like closures for special purposes; Border constructions therefor for protection against air-raid or other war-like action; for other protective purposes
- E06B5/16—Fireproof doors or similar closures; Adaptations of fixed constructions therefor
- E06B5/162—Fireproof doors having windows or other openings, e.g. for permitting ventilation or escape
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B3/00—Window sashes, door leaves, or like elements for closing wall or like openings; Layout of fixed or moving closures, e.g. windows in wall or like openings; Features of rigidly-mounted outer frames relating to the mounting of wing frames
- E06B3/54—Fixing of glass panes or like plates
- E06B3/58—Fixing of glass panes or like plates by means of borders, cleats, or the like
- E06B3/5892—Fixing of window panes in openings in door leaves
Landscapes
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Special Wing (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1041965A CH425164A (de) | 1965-07-21 | 1965-07-21 | Feuerhemmende Tür mit Fenster |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115758B true NO115758B (de) | 1968-11-25 |
Family
ID=4363027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16394666A NO115758B (de) | 1965-07-21 | 1966-07-15 |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT264798B (de) |
| BE (1) | BE683959A (de) |
| CH (1) | CH425164A (de) |
| DE (1) | DE1683055A1 (de) |
| DK (1) | DK109355C (de) |
| FI (1) | FI42134B (de) |
| GB (1) | GB1101287A (de) |
| LU (1) | LU51549A1 (de) |
| NL (1) | NL146252B (de) |
| NO (1) | NO115758B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH606749A5 (de) * | 1976-12-20 | 1978-11-15 | Inventio Ag | |
| WO1985000196A1 (en) * | 1983-06-20 | 1985-01-17 | Fire Research Pty. Limited | Fire windows |
| AT387261B (de) * | 1984-09-21 | 1988-12-27 | Lindpointner Tore | Tuer oder tor, insbesondere brandschutztor |
| US5367770A (en) * | 1993-05-03 | 1994-11-29 | Masco Industries, Inc. | Method for embossing indented door light opening edge |
| DE102004039416A1 (de) | 2004-04-14 | 2005-11-10 | Hörmann KG Freisen | Verglastes Feuerschutz-Türblatt sowie System und Verfahren zur Herstellung desselben |
| DE202012104484U1 (de) * | 2012-11-20 | 2014-02-25 | Holzbau Schmid Gmbh & Co. Kg | Mehrlagige Glasscheibe mit abgedecktem Randverbund |
| CN114776190A (zh) * | 2022-03-02 | 2022-07-22 | 安徽理工大学 | 一种防热辐射防火门 |
-
1965
- 1965-07-21 CH CH1041965A patent/CH425164A/de unknown
-
1966
- 1966-06-29 FI FI173266A patent/FI42134B/fi active
- 1966-07-08 DE DE19661683055 patent/DE1683055A1/de active Pending
- 1966-07-08 AT AT657366A patent/AT264798B/de active
- 1966-07-11 BE BE683959D patent/BE683959A/xx not_active IP Right Cessation
- 1966-07-12 NL NL6609783A patent/NL146252B/xx not_active IP Right Cessation
- 1966-07-13 LU LU51549D patent/LU51549A1/xx unknown
- 1966-07-15 NO NO16394666A patent/NO115758B/no unknown
- 1966-07-15 GB GB3185966A patent/GB1101287A/en not_active Expired
- 1966-07-20 DK DK378866A patent/DK109355C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| CH425164A (de) | 1966-11-30 |
| NL146252B (nl) | 1975-06-16 |
| DE1683055A1 (de) | 1970-04-30 |
| DK109355C (da) | 1968-04-16 |
| AT264798B (de) | 1968-09-10 |
| BE683959A (de) | 1967-01-11 |
| NL6609783A (de) | 1967-01-23 |
| LU51549A1 (de) | 1967-01-13 |
| FI42134B (de) | 1970-02-02 |
| GB1101287A (en) | 1968-01-31 |
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