SK11122001A3 - Spôsob prípravy 1,2,3,6-tetrahydro-2,2,6,6-tetraalkylpyridínov - Google Patents

Spôsob prípravy 1,2,3,6-tetrahydro-2,2,6,6-tetraalkylpyridínov Download PDF

Info

Publication number: SK11122001A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; metal oxide; water vapor; catalyst
Prior art date: 1999-02-05

Application number

SK1112-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Reinhard Sommerlade

Bernd Siebenhaar

Bruno Casagrande

Heinz Steiner

Original Assignee

Ciba Specialty Chemicals Holding Inc.

Priority date (The priority date 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 date listed.)

1999-02-05

Filing date

2000-01-31

Publication date

2001-12-03

2000-01-31 Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.

2001-12-03 Publication of SK11122001A3 publication Critical patent/SK11122001A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 41
230000008569 process Effects 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 14
239000003054 catalyst Substances 0.000 claims abstract description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
229910044991 metal oxide Inorganic materials 0.000 claims abstract description 25
150000004706 metal oxides Chemical class 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 18
239000007864 aqueous solution Substances 0.000 claims abstract description 15
239000007900 aqueous suspension Substances 0.000 claims abstract description 9
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 9
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 19
230000036571 hydration Effects 0.000 claims description 14
238000006703 hydration reaction Methods 0.000 claims description 14
230000018044 dehydration Effects 0.000 claims description 13
238000006297 dehydration reaction Methods 0.000 claims description 13
230000003647 oxidation Effects 0.000 claims description 13
238000007254 oxidation reaction Methods 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229910004298 SiO 2 Inorganic materials 0.000 claims description 7
229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 6
QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
229910052752 metalloid Inorganic materials 0.000 claims description 3
150000002738 metalloids Chemical class 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000004760 silicates Chemical class 0.000 claims description 3
239000004909 Moisturizer Substances 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
239000000499 gel Substances 0.000 claims description 2
230000001333 moisturizer Effects 0.000 claims description 2
238000005507 spraying Methods 0.000 claims description 2
239000010457 zeolite Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1,3-dihydropyridine Chemical compound CC1(C)CC=CC(C)(C)N1 ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000007800 oxidant agent Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
IBMCQJYLPXUOKM-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-3h-pyridine Chemical compound CN1C(C)(C)CC=CC1(C)C IBMCQJYLPXUOKM-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
HMIZIDZSHHZGOX-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1,3-dihydropyridine Chemical compound CCC1(C)NC(C)(CC)C(C)C=C1 HMIZIDZSHHZGOX-UHFFFAOYSA-N 0.000 description 3
-1 4-hydroxy-2 Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000007789 gas Substances 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
YSMAMMWBEBTNEH-UHFFFAOYSA-N [2-[2-[bis(phosphonomethyl)amino]ethoxy]ethyl-(phosphonomethyl)amino]methylphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCOCCN(CP(O)(O)=O)CP(O)(O)=O YSMAMMWBEBTNEH-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052593 corundum Inorganic materials 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
230000006698 induction Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
229910001845 yogo sapphire Inorganic materials 0.000 description 2
CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 1
TUGPREKSTXAQBY-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidin-4-ol Chemical compound CCC1(C)CC(O)C(C)C(C)(CC)N1 TUGPREKSTXAQBY-UHFFFAOYSA-N 0.000 description 1
PUVUYZAAQWYJNL-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidine Chemical compound CCC1(C)CCC(C)C(C)(CC)N1 PUVUYZAAQWYJNL-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
229910010413 TiO 2 Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
150000003869 acetamides Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003990 capacitor Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000008859 change Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000005373 porous glass Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000758 substrate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1112-2001A 1999-02-05 2000-01-31 Spôsob prípravy 1,2,3,6-tetrahydro-2,2,6,6-tetraalkylpyridínov SK11122001A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH21999		1999-02-05
CH48499		1999-03-16
PCT/EP2000/000733 WO2000046202A2 (en)	1999-02-05	2000-01-31	Process for the preparation of 1,2,3,6-tetrahydro-2,2,6,6-tetraalkylpyridines

Publications (1)

Publication Number	Publication Date
SK11122001A3 true SK11122001A3 (sk)	2001-12-03

Family

ID=25683917

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1112-2001A SK11122001A3 (sk)	1999-02-05	2000-01-31	Spôsob prípravy 1,2,3,6-tetrahydro-2,2,6,6-tetraalkylpyridínov

Country Status (9)

Country	Link
EP (1)	EP1144378A3 (cs)
JP (1)	JP2002536363A (cs)
KR (1)	KR20010089632A (cs)
CN (1)	CN1352633A (cs)
AU (1)	AU2905900A (cs)
CA (1)	CA2352507A1 (cs)
CZ (1)	CZ20012808A3 (cs)
SK (1)	SK11122001A3 (cs)
WO (1)	WO2000046202A2 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010112410A1 (en)	2009-03-30	2010-10-07	Basf Se	Polymerizable compositions
CN102241623A (zh) *	2010-05-13	2011-11-16	上海医药工业研究院	一类n-取代-4-卤代烷基哌啶醇类衍生物及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0157738B1 (de) *	1984-03-22	1989-04-19	Ciba-Geigy Ag	Verfahren zur Herstellung von Nitroxylen sterisch gehinderter Amine
DE19711226A1 (de) *	1997-03-18	1998-09-24	Huels Chemische Werke Ag	Verfahren zur Herstellung von 1,2,3,6-Tetrahydro-2,2,6,6-tetramethylpyridin-N-oxyl
DE19732589A1 (de) *	1997-07-29	1999-02-04	Huels Chemische Werke Ag	Verfahren zur Herstellung von 1,2,3,6-tetrahydro-2,2,6,6-tetramethylpyridin

2000
- 2000-01-31 CZ CZ20012808A patent/CZ20012808A3/cs unknown
- 2000-01-31 WO PCT/EP2000/000733 patent/WO2000046202A2/en not_active Ceased
- 2000-01-31 SK SK1112-2001A patent/SK11122001A3/sk unknown
- 2000-01-31 KR KR1020017009833A patent/KR20010089632A/ko not_active Withdrawn
- 2000-01-31 CA CA002352507A patent/CA2352507A1/en not_active Abandoned
- 2000-01-31 CN CN00803344A patent/CN1352633A/zh active Pending
- 2000-01-31 AU AU29059/00A patent/AU2905900A/en not_active Abandoned
- 2000-01-31 EP EP00907490A patent/EP1144378A3/en not_active Withdrawn
- 2000-01-31 JP JP2000597272A patent/JP2002536363A/ja active Pending

Also Published As

Publication number	Publication date
AU2905900A (en)	2000-08-25
EP1144378A2 (en)	2001-10-17
WO2000046202A3 (en)	2001-12-06
JP2002536363A (ja)	2002-10-29
CN1352633A (zh)	2002-06-05
EP1144378A3 (en)	2002-09-11
KR20010089632A (ko)	2001-10-06
WO2000046202A2 (en)	2000-08-10
CZ20012808A3 (cs)	2001-11-14
CA2352507A1 (en)	2000-08-10

Publication	Publication Date	Title
MX2008016304A (es)	2009-01-16	Proceso para la preparacion de nitroxil eteres impedidos estericamente.
IE862605L (en)	1987-04-28	Preparation of disubstituted pyridine -2,3- dicarboxylates
US5728836A (en)	1998-03-17	Process for preparing 4-acylamino-2,2,6,6-tetramethylpiperidines
EP0488403B1 (en)	1995-10-25	Process for the preparation of nitroxyl radicals of sterically hindered amines
JPH0560464B2 (cs)	1993-09-02
US8318942B2 (en)	2012-11-27	Process for preparing Donepezil and its derivatives
JP6188506B2 (ja)	2017-08-30	トリアセトンアミン含有反応混合物の製造法及び後処理法
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