FI61311C - Nytt foerfarande foer framstaellning av 2-acylamino-bentsylaminer - Google Patents
Nytt foerfarande foer framstaellning av 2-acylamino-bentsylaminer Download PDFInfo
- Publication number
- FI61311C FI61311C FI1775/74A FI177574A FI61311C FI 61311 C FI61311 C FI 61311C FI 1775/74 A FI1775/74 A FI 1775/74A FI 177574 A FI177574 A FI 177574A FI 61311 C FI61311 C FI 61311C
- Authority
- FI
- Finland
- Prior art keywords
- tai
- hai
- yleiskaavan
- jossa
- menetelmä
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 9
- -1 cyclohexyl- Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- UBKQQWZEERYSOW-UHFFFAOYSA-N 5-chloro-2-phenyl-4H-3,1-benzoxazine Chemical compound ClC1=CC=CC2=C1COC(=N2)C2=CC=CC=C2 UBKQQWZEERYSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 description 1
- HEPOIJKOXBKKNJ-UHFFFAOYSA-N 2-(propan-2-ylazaniumyl)acetate Chemical compound CC(C)NCC(O)=O HEPOIJKOXBKKNJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VNGWVUIEAJNWDT-UHFFFAOYSA-N 5-bromo-2-phenyl-4H-3,1-benzoxazine Chemical compound BrC1=CC=CC2=C1COC(=N2)C2=CC=CC=C2 VNGWVUIEAJNWDT-UHFFFAOYSA-N 0.000 description 1
- DKWARGDCHPXUDA-UHFFFAOYSA-N 7-chloro-2-phenyl-4H-3,1-benzoxazine Chemical compound C1(=CC=CC=C1)C1=NC2=C(CO1)C=CC(=C2)Cl DKWARGDCHPXUDA-UHFFFAOYSA-N 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- ZZQSFFNQYSNMBT-UHFFFAOYSA-N N-[2,4-dibromo-6-[[methyl-(2-morpholin-4-yl-2-oxoethyl)amino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)N2CCOCC2)C)C=C(C=C1Br)Br ZZQSFFNQYSNMBT-UHFFFAOYSA-N 0.000 description 1
- UWLSVPWMRKMJNO-UHFFFAOYSA-N N-[3-bromo-2-[[methyl-(2-morpholin-2-yl-2-oxoethyl)amino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)C2CNCCO2)C)C(=CC=C1)Br UWLSVPWMRKMJNO-UHFFFAOYSA-N 0.000 description 1
- DFDUDRITYNZCLP-UHFFFAOYSA-N N-[3-chloro-2-[[(2-morpholin-4-yl-2-oxoethyl)-propan-2-ylamino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)N2CCOCC2)C(C)C)C(=CC=C1)Cl DFDUDRITYNZCLP-UHFFFAOYSA-N 0.000 description 1
- WLMVUCVOAJYFKF-UHFFFAOYSA-N N-[5-chloro-2-[[methyl-[2-oxo-2-(propan-2-ylamino)ethyl]amino]methyl]phenyl]benzamide Chemical compound C(C)(C)NC(CN(C)CC1=C(C=C(C=C1)Cl)NC(C1=CC=CC=C1)=O)=O WLMVUCVOAJYFKF-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000005130 benzoxazines Chemical group 0.000 description 1
- KSNNEUZOAFRTDS-UHFFFAOYSA-N fominoben Chemical compound ClC=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1CN(C)CC(=O)N1CCOCC1 KSNNEUZOAFRTDS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- SSISCWJZVJGIHM-UHFFFAOYSA-N n-[2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]phenyl]benzamide Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1NC(=O)C1=CC=CC=C1 SSISCWJZVJGIHM-UHFFFAOYSA-N 0.000 description 1
- GPDRKPABYHURLK-UHFFFAOYSA-N n-[2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]phenyl]benzamide;hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1NC(=O)C1=CC=CC=C1 GPDRKPABYHURLK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732337456 DE2337456A1 (de) | 1973-07-24 | 1973-07-24 | Neues verfahren zur herstellung von 2-acylamino-benzylaminen |
| DE2337456 | 1973-07-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI177574A7 FI177574A7 (enrdf_load_stackoverflow) | 1975-01-25 |
| FI61311B FI61311B (fi) | 1982-03-31 |
| FI61311C true FI61311C (fi) | 1982-07-12 |
Family
ID=5887784
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1775/74A FI61311C (fi) | 1973-07-24 | 1974-06-11 | Nytt foerfarande foer framstaellning av 2-acylamino-bentsylaminer |
| FI801782A FI801782A7 (fi) | 1973-07-24 | 1980-06-03 | Bentsoksatsiini, joka on lähtöaine valmistettaessa farmaseuttisesti arvokkaita 2-asyyliamino-bentsyyliamibentsyyliamiineja sekä menetelmä sen valmistamiseksi. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801782A FI801782A7 (fi) | 1973-07-24 | 1980-06-03 | Bentsoksatsiini, joka on lähtöaine valmistettaessa farmaseuttisesti arvokkaita 2-asyyliamino-bentsyyliamibentsyyliamiineja sekä menetelmä sen valmistamiseksi. |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6378894B2 (ja) * | 2014-02-27 | 2018-08-22 | 国立大学法人東京工業大学 | トリフルオロメチル基含有オキサジン類及びその製造方法 |
-
1974
- 1974-06-11 FI FI1775/74A patent/FI61311C/fi active
- 1974-06-20 AT AT510774A patent/AT333262B/de not_active IP Right Cessation
- 1974-06-26 BG BG027081A patent/BG23744A3/xx unknown
- 1974-07-01 YU YU01844/74A patent/YU36366B/xx unknown
- 1974-07-04 ES ES0427951A patent/ES427951A1/es not_active Expired
- 1974-07-18 NL NL7409722A patent/NL7409722A/xx not_active Application Discontinuation
- 1974-07-22 HU HUTO970A patent/HU167972B/hu unknown
- 1974-07-22 CH CH1453677A patent/CH605866A5/xx not_active IP Right Cessation
- 1974-07-22 CH CH1007774A patent/CH603562A5/xx not_active IP Right Cessation
- 1974-07-23 SE SE7409585A patent/SE413893B/xx unknown
- 1974-07-23 JP JP49084539A patent/JPS5817456B2/ja not_active Expired
- 1974-07-23 PL PL1974172935A patent/PL91391B1/pl unknown
- 1974-07-23 CA CA205,415A patent/CA1050544A/en not_active Expired
- 1974-07-23 DK DK396774A patent/DK140009C/da not_active IP Right Cessation
-
1977
- 1977-04-06 SE SE7704094A patent/SE7704094L/xx unknown
-
1980
- 1980-06-03 FI FI801782A patent/FI801782A7/fi not_active Application Discontinuation
-
1982
- 1982-11-15 JP JP57200254A patent/JPS6027672B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK140009B (da) | 1979-06-05 |
| SE413893B (sv) | 1980-06-30 |
| FI61311B (fi) | 1982-03-31 |
| HU167972B (en) | 1976-01-28 |
| JPS58154563A (ja) | 1983-09-14 |
| ATA510774A (de) | 1976-03-15 |
| DK140009C (da) | 1979-11-05 |
| YU184474A (en) | 1981-11-13 |
| JPS5817456B2 (ja) | 1983-04-07 |
| ES427951A1 (es) | 1976-09-01 |
| FI801782A7 (fi) | 1981-01-01 |
| AT333262B (de) | 1976-11-10 |
| CH603562A5 (en) | 1978-08-31 |
| PL91391B1 (enrdf_load_stackoverflow) | 1977-02-28 |
| DK396774A (enrdf_load_stackoverflow) | 1975-03-10 |
| NL7409722A (nl) | 1975-01-28 |
| SE7704094L (sv) | 1977-04-06 |
| JPS6027672B2 (ja) | 1985-06-29 |
| FI177574A7 (enrdf_load_stackoverflow) | 1975-01-25 |
| BG23744A3 (bg) | 1977-10-12 |
| CA1050544A (en) | 1979-03-13 |
| YU36366B (en) | 1983-06-30 |
| CH605866A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| SE7409585L (sv) | 1975-01-27 |
| JPS5041834A (enrdf_load_stackoverflow) | 1975-04-16 |
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