NO119899B - - Google Patents
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- Publication number
- NO119899B NO119899B NO156815A NO15681565A NO119899B NO 119899 B NO119899 B NO 119899B NO 156815 A NO156815 A NO 156815A NO 15681565 A NO15681565 A NO 15681565A NO 119899 B NO119899 B NO 119899B
- Authority
- NO
- Norway
- Prior art keywords
- amino
- methyl
- piperidine
- benzoyl
- solution
- Prior art date
Links
- -1 1-methyl-4-(p-nitrobenzoyl)-amino-piperidine Chemical compound 0.000 claims description 5
- IPABBONWZVMTSS-UHFFFAOYSA-N CN1C(CC(CC1)C(C1=CC=C(C=C1)N)=O)N Chemical compound CN1C(CC(CC1)C(C1=CC=C(C=C1)N)=O)N IPABBONWZVMTSS-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001122767 Theaceae Species 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G47/00—Article or material-handling devices associated with conveyors; Methods employing such devices
- B65G47/74—Feeding, transfer, or discharging devices of particular kinds or types
- B65G47/84—Star-shaped wheels or devices having endless travelling belts or chains, the wheels or devices being equipped with article-engaging elements
- B65G47/846—Star-shaped wheels or wheels equipped with article-engaging elements
- B65G47/847—Star-shaped wheels or wheels equipped with article-engaging elements the article-engaging elements being grippers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B41/00—Component parts such as frames, beds, carriages, headstocks
- B24B41/005—Feeding or manipulating devices specially adapted to grinding machines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B7/00—Machines or devices designed for grinding plane surfaces on work, including polishing plane glass surfaces; Accessories therefor
- B24B7/20—Machines or devices designed for grinding plane surfaces on work, including polishing plane glass surfaces; Accessories therefor characterised by a special design with respect to properties of the material of non-metallic articles to be ground
- B24B7/22—Machines or devices designed for grinding plane surfaces on work, including polishing plane glass surfaces; Accessories therefor characterised by a special design with respect to properties of the material of non-metallic articles to be ground for grinding inorganic material, e.g. stone, ceramics, porcelain
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28D—WORKING STONE OR STONE-LIKE MATERIALS
- B28D1/00—Working stone or stone-like materials, e.g. brick, concrete or glass, not provided for elsewhere; Machines, devices, tools therefor
- B28D1/18—Working stone or stone-like materials, e.g. brick, concrete or glass, not provided for elsewhere; Machines, devices, tools therefor by milling, e.g. channelling by means of milling tools
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28D—WORKING STONE OR STONE-LIKE MATERIALS
- B28D7/00—Accessories specially adapted for use with machines or devices of the preceding groups
- B28D7/04—Accessories specially adapted for use with machines or devices of the preceding groups for supporting or holding work or conveying or discharging work
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Mining & Mineral Resources (AREA)
- Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Inorganic Chemistry (AREA)
- Grinding Of Cylindrical And Plane Surfaces (AREA)
- Hydrogenated Pyridines (AREA)
- Devices For Post-Treatments, Processing, Supply, Discharge, And Other Processes (AREA)
Description
Fremgangsmåte for fremstilling av l-metyl-4-(p-amino-bensoyl)-amino - piperidin. Process for the production of 1-methyl-4-(p-amino-benzoyl)-amino-piperidine.
Det har vist seg at det kan oppnås 1-metyl-4- (p-amino-bensoyl) -amino-piperi-din med formelen It has been found that 1-methyl-4-(p-amino-benzoyl)-amino-piperidine can be obtained with the formula
ved at nitrogruppen i l-metyl-4-(p-nitro-bensoyl)-aminopiperidin reduseres til aminogruppe ved hjelp av katalytisk aktivert in that the nitro group in l-methyl-4-(p-nitro-benzoyl)-aminopiperidine is reduced to an amino group by means of catalytically activated
vannstoff. water substance.
Fremgangsmåten kan eksempelvis ut-føres slik at det l-metyl-4-(p-nitro-bensoyl)-amino-piperidin som kan fremstilles slik som angitt i patent nr. 87 451, reduseres i alkoholisk oppløsning ved værelsestemperatur med vannstoff som er aktivi-sert katalytisk. The method can, for example, be carried out so that the 1-methyl-4-(p-nitro-benzoyl)-amino-piperidine, which can be prepared as stated in patent no. 87 451, is reduced in an alcoholic solution at room temperature with hydrogen which is active -sert catalytic.
Det l-metyl-4-(p-amino-bensoyl)-amino-piperidin som fremstilles i henhold til The 1-methyl-4-(p-amino-benzoyl)-amino-piperidine prepared according to
foreliggende oppfinnelse er en base som er the present invention is a base which is
krystallisert ved værelsestemperatur og som crystallized at room temperature and as
med syrer danner varige salter. with acids form permanent salts.
Sluttproduktet har terapeutisk verdi-fulle farmakodynamiske egenskaper. Det The end product has therapeutically valuable pharmacodynamic properties. The
gjør h jer tevirksomheten regelmessig og do h jer tea business regularly and
skal i terapien benyttes til å bekjempe must be used in the therapy to combat
hjertearrytmi, spesielt når denne opptrer cardiac arrhythmia, especially when this occurs
under operasjoner, f. eks. som sidevirkning during operations, e.g. as a side effect
av narkotika. of drugs.
Eksempel: Example:
En oppløsning av 32,0 g l-metyl-4- amino-piperidin i 250 cm<3> bensol blir ved værelsestemperatur dråpevis biandet med en oppløsning av 55.0 g p-nitro-bensoyl-klorid i 250 cm<8> bensol, og blandingen får stå i 12 timer. Blandingen blir rystet ut med 300 cm<8> 1,5-n saltsyre, og det vandige saltsure lag blandet med natronlut til fenolftalein-alkalisk reaksjon. Det utfeldte l-metyl-4-(p-nitro-bensoyl)-amino-pipe-ridin blir sudd bort og omkrystallisert fra en kokende blanding av aceton og etanol (7 : 3). Smp. 197-198°. Oppløsningen av 19,0 g l-metyl-4-(p-nitro-bensoyl)-amino-piperidin i 400 cm<8 >abs etanol og 50 cm'<1> 36 pst. saltsyre blir hydrert ved værelsestemperatur i nærvær av 40 g fuktig palladiumkull (tilsvarende 800 mg palladium-metall) i løpet av ca. iy2 time. Den oppløsning som filtreres av fra katalysatoren blir inndampet i vakuum ved 50°, og oppløsningen av resten i 400 cm<s> vann blir blandet med 3-n natronlut til fenolftalein-alkalisk reaksjon. Den ut-skilte base, l-metyl-4-(p-amino-bensoyl)-amino-piperidin, har etter omkrystallise-ring fra den 18-dobbelte mengde av en blanding av aceton og vann (1 : 1) et smel-tepunkt på 195—197. For å fremstille hydrokloridet dampes oppløsningen av den fri base i den ekviva-lente mengde l-n saltsyre inn i vakuum ved 50° til tørr tilstand, og oppløsningen av resten i den 40-dobbelte mengde abs. alko- hol blandes med den 30-dobbelte mengder eter, hvorved l-metyl-4- (p-amino-bensoyl) -amino-piperidin-hydroklorid skiller seg ut krystallinsk. Smp. 188—190°. A solution of 32.0 g of l-methyl-4- amino-piperidine in 250 cm<3> benzene remains room temperature is mixed dropwise with a solution of 55.0 g of p-nitro-benzoyl chloride in 250 cm<8> of benzene, and the mixture is allowed to stand for 12 hours. The mixture is shaken out with 300 cm<8> of 1.5-n hydrochloric acid, and the aqueous hydrochloric acid layer is mixed with caustic soda for a phenolphthalein-alkaline reaction. It precipitated 1-methyl-4-(p-nitro-benzoyl)-amino-piperidine is washed away and recrystallized from a boiling mixture of acetone and ethanol (7:3). Temp. 197-198°. The solution of 19.0 g of 1-methyl-4-(p-nitro-benzoyl)-amino-piperidine in 400 cm<8 >abs ethanol and 50 cm'<1> 36% hydrochloric acid is hydrated at room temperature in the presence of 40 g moist palladium charcoal (equivalent to 800 mg palladium metal) during approx. iy2 hours. The solution filtered off from the catalyst is evaporated in vacuo at 50°, and the solution of the residue in 400 cm<s> of water is mixed with 3-n caustic soda for a phenolphthalein-alkaline reaction. The precipitated base, 1-methyl-4-(p-amino-benzoyl)-amino-piperidine, after recrystallization from the 18-fold amount of a mixture of acetone and water (1:1) has a melting tea point of 195-197. To prepare the hydrochloride, the solution of the free base in the equivalent amount of 1-n hydrochloric acid is evaporated in vacuo at 50° to a dry state, and the solution of the residue in the 40-fold amount of abs. alcohol hol is mixed with the 30-fold amount of ether, whereby 1-methyl-4-(p-amino-benzoyl)-amino-piperidine hydrochloride separates out crystalline. Temp. 188-190°.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346339A US3292310A (en) | 1964-02-20 | 1964-02-20 | Apparatus for grinding bricks or the like |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119899B true NO119899B (en) | 1970-07-20 |
Family
ID=23358936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO156815A NO119899B (en) | 1964-02-20 | 1965-02-17 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3292310A (en) |
| AT (1) | AT258752B (en) |
| BE (1) | BE659451A (en) |
| CH (1) | CH427548A (en) |
| DE (1) | DE1502456A1 (en) |
| DK (1) | DK108956C (en) |
| ES (1) | ES309951A1 (en) |
| FR (1) | FR1433414A (en) |
| GB (1) | GB1067604A (en) |
| NL (1) | NL6502089A (en) |
| NO (1) | NO119899B (en) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410259A (en) * | 1965-09-14 | 1968-11-12 | Skirvin Walter | Brick cleaning device |
| DE2510827C2 (en) * | 1975-03-12 | 1977-02-24 | Badische Maschf Gmbh | CONVEYOR DEVICE FOR CYLINDER BLOCKS OR SIMILAR WORKPIECES BY A SPIN BLASTING SYSTEM |
| US4256078A (en) * | 1979-11-13 | 1981-03-17 | The R. T. French Co. | Brick finishing machine |
| US4660539A (en) * | 1985-06-04 | 1987-04-28 | Battaglia Gino C | Method and apparatus for cutting and polishing marble slabs |
| DE3843379A1 (en) * | 1988-12-23 | 1990-07-05 | Raimund Rimmele | Method of manufacturing precisely plane-parallel bricks |
| DE3928328C1 (en) * | 1989-08-26 | 1990-12-20 | Keuro Maschinenbau Gmbh & Co Kg, 7590 Achern, De | |
| NL192608C (en) * | 1990-07-06 | 1997-11-04 | Boer Beheer Nijmegen Bv De | Device for manufacturing clay bricks. |
| AT400828B (en) * | 1993-12-30 | 1996-03-25 | Kamas Maschinen Und Stahlbau G | Method and installation for manufacturing ceramic tiles with great dimensional accuracy |
| DE4436148C1 (en) * | 1994-10-11 | 1996-07-04 | Keller Gmbh | Method and device for the lateral leveling of brick moldings and / or bricks |
| DE19601723A1 (en) * | 1996-01-18 | 1997-07-24 | Klinkerwerk Hagemeister Gmbh & | Paving or facing stone with stone-demarcating side spacers |
| US20030079586A1 (en) * | 2001-10-25 | 2003-05-01 | John Zukley | Brick recycling method and apparatus |
| US6736127B2 (en) * | 2002-01-31 | 2004-05-18 | Joseph M. Steckling | Inline pitching system |
| BE1016281A3 (en) * | 2004-03-05 | 2006-07-04 | Aelst Filip Van | METHOD AND DEVICE FOR CUTTING BLOCKS OF NATURAL STONE. |
| US20060037267A1 (en) * | 2004-08-05 | 2006-02-23 | Taylor Charles D Jr | Simulated granite |
| CN104290000B (en) * | 2014-09-26 | 2016-07-27 | 浙江海洋学院 | A kind of vehicle oil filler cover plate finishing machine |
| CN107443353A (en) * | 2016-05-30 | 2017-12-08 | 洛阳海特智能科技有限公司 | A kind of wall-building robot and its method of work |
| WO2018009981A1 (en) | 2016-07-15 | 2018-01-18 | Fastbrick Ip Pty Ltd | Brick/block laying machine incorporated in a vehicle |
| US10865578B2 (en) | 2016-07-15 | 2020-12-15 | Fastbrick Ip Pty Ltd | Boom for material transport |
| EP3649616A4 (en) | 2017-07-05 | 2021-04-07 | Fastbrick IP Pty Ltd | Real time position and orientation tracker |
| US10301121B1 (en) * | 2017-07-20 | 2019-05-28 | Amazon Technologies, Inc. | System having a carousel of buckets configured to induct inventory items into packaging |
| WO2019033165A1 (en) | 2017-08-17 | 2019-02-21 | Fastbrick Ip Pty Ltd | Interaction system configuration |
| AU2018348785B2 (en) | 2017-10-11 | 2024-05-02 | Fastbrick Ip Pty Ltd | Machine for conveying objects and multi-bay carousel for use therewith |
| CN108422574A (en) * | 2018-05-11 | 2018-08-21 | 广西钟山县天顺石材有限公司 | A kind of positioning device of plate cutting |
| CN109605206B (en) * | 2018-12-29 | 2024-07-19 | 慈兴集团有限公司 | Bearing inner ring superfine grinding device and method with outer diameter positioning function |
| CN110524253B (en) * | 2019-08-23 | 2024-05-10 | 宝鸡保德利电气设备有限责任公司 | Automatic polishing equipment for high-speed rail contact net aluminum alloy parts |
| CN111113239A (en) * | 2020-01-08 | 2020-05-08 | 佛山瑞萨纳建材有限公司 | Polishing machine |
| CN112045519A (en) * | 2020-07-31 | 2020-12-08 | 山东高强紧固件有限公司 | Bolt thread processing equipment |
| CN112658902B (en) * | 2021-01-25 | 2023-06-23 | 广东顺德川崎汽车零部件有限公司 | Vibration damper surface polishing device for new energy automobile processing |
| CN113120592A (en) * | 2021-04-19 | 2021-07-16 | 仪征海天铝业有限公司 | Finned tube recovery device |
| CN113319667B (en) * | 2021-05-27 | 2022-05-24 | 诸暨市金科弹簧科技有限公司 | Spring end surface grinding machine |
| CN113333611B (en) * | 2021-06-19 | 2022-09-23 | 芜湖常瑞汽车部件有限公司 | Automobile part production line conveying and circulating device |
| CN114055311B (en) * | 2022-01-05 | 2022-03-25 | 烟台奥森制动材料有限公司 | Multi-grinding-head multi-angle quick grinding device for grinding carbon-carbon crucible |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US406450A (en) * | 1889-07-09 | la casse | ||
| US1646359A (en) * | 1927-10-18 | Island | ||
| US766403A (en) * | 1904-03-01 | 1904-08-02 | Miquel Vincke & Meyer | Machine for grinding corks simultaneously on both ends and forming them same length. |
| US1166647A (en) * | 1907-11-05 | 1916-01-04 | Huntley Mfg Company | Corn-husking machine. |
| US2000458A (en) * | 1934-05-17 | 1935-05-07 | Wood Preserving Corp | Adzing and boring machine |
| US2352551A (en) * | 1942-03-02 | 1944-06-27 | Universal Camera Corp | Method of forming optical prisms |
| US2799124A (en) * | 1955-06-10 | 1957-07-16 | Dean A Polzin | Conveyor system for pistons to and from grinding machines |
-
1964
- 1964-02-20 US US346339A patent/US3292310A/en not_active Expired - Lifetime
-
1965
- 1965-02-08 FR FR4726A patent/FR1433414A/en not_active Expired
- 1965-02-09 BE BE659451D patent/BE659451A/xx unknown
- 1965-02-09 CH CH172065A patent/CH427548A/en unknown
- 1965-02-12 AT AT128065A patent/AT258752B/en active
- 1965-02-17 NO NO156815A patent/NO119899B/no unknown
- 1965-02-17 GB GB6748/65A patent/GB1067604A/en not_active Expired
- 1965-02-17 DE DE1965I0027523 patent/DE1502456A1/en active Pending
- 1965-02-19 DK DK88465AA patent/DK108956C/en active
- 1965-02-19 NL NL6502089A patent/NL6502089A/xx unknown
- 1965-02-20 ES ES309951A patent/ES309951A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1067604A (en) | 1967-05-03 |
| DE1502456A1 (en) | 1969-04-10 |
| ES309951A1 (en) | 1965-11-16 |
| NL6502089A (en) | 1965-08-23 |
| DK108956C (en) | 1968-02-26 |
| BE659451A (en) | 1965-08-09 |
| CH427548A (en) | 1966-12-31 |
| US3292310A (en) | 1966-12-20 |
| AT258752B (en) | 1967-12-11 |
| FR1433414A (en) | 1966-04-01 |
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