SK4262000A3 - Method for purifying 4-amino-piperidines - Google Patents

Method for purifying 4-amino-piperidines Download PDF

Info

Publication number: SK4262000A3
Authority: SK; Slovakia
Prior art keywords: reaction; aminopiperidines; process according; hydrogenation; aminopiperidine
Prior art date: 1997-10-01

Application number

SK426-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Manfred Julius

Hardo Siegel

Tom Witzel

Wolfgang Siegel

Original Assignee

Basf Ag

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.)

1997-10-01

Filing date

1998-09-25

Publication date

2000-10-09

1998-09-25 Application filed by Basf Ag filed Critical Basf Ag

2000-10-09 Publication of SK4262000A3 publication Critical patent/SK4262000A3/sk

Links

BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical class NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 title claims abstract description 32
238000000034 method Methods 0.000 title claims abstract description 28
239000003054 catalyst Substances 0.000 claims abstract description 26
238000004821 distillation Methods 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims abstract description 8
-1 2,2,6,6-tetrasubstituted 4-amino-piperidines Chemical class 0.000 claims abstract description 6
239000011541 reaction mixture Substances 0.000 claims abstract description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 18
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 10
229910052802 copper Inorganic materials 0.000 claims description 8
239000010949 copper Substances 0.000 claims description 8
238000000746 purification Methods 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
229910017052 cobalt Inorganic materials 0.000 claims description 5
239000010941 cobalt Substances 0.000 claims description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
238000006356 dehydrogenation reaction Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
229910052737 gold Inorganic materials 0.000 claims description 2
239000010931 gold Substances 0.000 claims description 2
229910052741 iridium Inorganic materials 0.000 claims description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052750 molybdenum Inorganic materials 0.000 claims description 2
239000011733 molybdenum Substances 0.000 claims description 2
229910052762 osmium Inorganic materials 0.000 claims description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
229910052702 rhenium Inorganic materials 0.000 claims description 2
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
229910052703 rhodium Inorganic materials 0.000 claims 1
239000010948 rhodium Substances 0.000 claims 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
229910001928 zirconium oxide Inorganic materials 0.000 claims 1
230000000887 hydrating effect Effects 0.000 abstract 1
241001550224 Apha Species 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000002360 preparation method Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000002638 heterogeneous catalyst Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000005576 amination reaction Methods 0.000 description 3
238000004042 decolorization Methods 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
150000003053 piperidines Chemical class 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
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 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Inorganic materials O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910001845 yogo sapphire Inorganic materials 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910052726 zirconium Inorganic materials 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
- C07D211/06—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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached 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
- C07D211/04—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK426-2000A 1997-10-01 1998-09-25 Method for purifying 4-amino-piperidines SK4262000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19743433A DE19743433C1 (de)	1997-10-01	1997-10-01	Verfahren zur Reinigung von 4-Amino-piperidinen
PCT/EP1998/006117 WO1999016749A1 (de)	1997-10-01	1998-09-25	Verfahren zur reinigung von 4-amino-piperidinen

Publications (1)

Publication Number	Publication Date
SK4262000A3 true SK4262000A3 (en)	2000-10-09

Family

ID=7844311

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK426-2000A SK4262000A3 (en)	1997-10-01	1998-09-25	Method for purifying 4-amino-piperidines

Country Status (16)

Country	Link
EP (1)	EP1025084A1 (id)
JP (1)	JP2001518465A (id)
KR (1)	KR20010030840A (id)
CN (1)	CN1272843A (id)
AU (1)	AU9746998A (id)
BR (1)	BR9812595A (id)
CA (1)	CA2305282A1 (id)
CO (1)	CO4770994A1 (id)
DE (1)	DE19743433C1 (id)
HU (1)	HUP0004584A2 (id)
ID (1)	ID23897A (id)
NZ (1)	NZ503565A (id)
PL (1)	PL339578A1 (id)
SK (1)	SK4262000A3 (id)
TW (1)	TW377345B (id)
WO (1)	WO1999016749A1 (id)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102008040045A1 (de) *	2008-02-01	2009-08-06	Evonik Degussa Gmbh	Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin
EP2085384A1 (de)	2008-02-01	2009-08-05	Evonik Degussa GmbH	Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3003843A1 (de) *	1980-02-02	1981-08-13	Chemische Werke Hüls AG, 4370 Marl	Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin
CH664361A5 (de) *	1985-06-13	1988-02-29	Ni Institutkhimikatov Dlya Pol	Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin.
US4766247A (en) *	1986-09-26	1988-08-23	Air Products And Chemicals, Inc.	Color reduction of polyamines by mild catalytic hydrogenation
JP2718179B2 (ja) *	1989-05-26	1998-02-25	三井化学株式会社	２，２，６，６‐テトラアルキル‐４‐ピペリジノンの精製方法
DE19622269A1 (de) *	1996-06-03	1997-12-04	Basf Ag	Verfahren zur Reinigung von sterisch gehinderten 4-Aminopiperidinen

1997
- 1997-10-01 DE DE19743433A patent/DE19743433C1/de not_active Expired - Lifetime
1998
- 1998-09-25 WO PCT/EP1998/006117 patent/WO1999016749A1/de not_active Ceased
- 1998-09-25 CA CA002305282A patent/CA2305282A1/en not_active Abandoned
- 1998-09-25 KR KR1020007003498A patent/KR20010030840A/ko not_active Withdrawn
- 1998-09-25 HU HU0004584A patent/HUP0004584A2/hu unknown
- 1998-09-25 JP JP2000513835A patent/JP2001518465A/ja not_active Withdrawn
- 1998-09-25 CN CN98809761A patent/CN1272843A/zh active Pending
- 1998-09-25 AU AU97469/98A patent/AU9746998A/en not_active Abandoned
- 1998-09-25 ID IDW20000612D patent/ID23897A/id unknown
- 1998-09-25 EP EP98951469A patent/EP1025084A1/de not_active Withdrawn
- 1998-09-25 SK SK426-2000A patent/SK4262000A3/sk unknown
- 1998-09-25 PL PL98339578A patent/PL339578A1/xx unknown
- 1998-09-25 BR BR9812595-8A patent/BR9812595A/pt not_active Application Discontinuation
- 1998-09-25 NZ NZ503565A patent/NZ503565A/en unknown
- 1998-09-30 TW TW087116216A patent/TW377345B/zh active
- 1998-09-30 CO CO98056932A patent/CO4770994A1/es unknown

Also Published As

Publication number	Publication date
TW377345B (en)	1999-12-21
HUP0004584A2 (hu)	2001-04-28
WO1999016749A1 (de)	1999-04-08
CN1272843A (zh)	2000-11-08
NZ503565A (en)	2001-09-28
EP1025084A1 (de)	2000-08-09
CO4770994A1 (es)	1999-04-30
KR20010030840A (ko)	2001-04-16
BR9812595A (pt)	2000-08-01
ID23897A (id)	2000-05-25
DE19743433C1 (de)	1999-04-22
CA2305282A1 (en)	1999-04-08
JP2001518465A (ja)	2001-10-16
PL339578A1 (en)	2000-12-18
AU9746998A (en)	1999-04-23

Publication	Publication Date	Title
US4605743A (en)	1986-08-12	Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines
US20030130313A1 (en)	2003-07-10	Processes for producing racemic piperidine derivative and for producing optically active piperidine derivative
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EP0611137B1 (en)	1996-04-24	Process for producing amines starting from cyclic ketones
CA1336604C (en)	1995-08-08	Process for the preparation of bis(2,2,6,6-tetramethyl-4-piperidyl)amine
SK4262000A3 (en)	2000-10-09	Method for purifying 4-amino-piperidines
TWI449694B (zh)	2014-08-21	４－胺基－２，２，６，６－四甲基哌啶的製備方法
MXPA00002989A (en)	2001-06-26	Method for purifying 4-amino-piperidines
CZ20001042A3 (cs)	2000-07-12	Způsob čištění 4-amino-piperidinů
AU711518B2 (en)	1999-10-14	Sterically hindered 4-aminopiperidines having a reduced dimer content, their preparation and their use
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KR100458246B1 (ko)	2005-06-27	이량체함량이낮은입체적으로차폐된4-아미노-피페리딘,그의제조방법및용도
JPS6134412B2 (id)	1986-08-07
EP0757989A1 (en)	1997-02-12	A process for producing octahydrocoumarins and same as a product of such process
WO2000012476A9 (en)	2000-10-05	Processes for preparing 2-piperidineethanol compounds
KR20040031989A (ko)	2004-04-14	4-아미노-1-부탄올의 제조방법
JP2003192668A (ja)	2003-07-09	光学活性３−アルコキシカルボニルアミノピロリジン誘導体の製造方法