EP1776341A1 - Verfahren zur herstellung von n-aminopiperidin und seinen salzen - Google Patents

Verfahren zur herstellung von n-aminopiperidin und seinen salzen

Info

Publication number
EP1776341A1
EP1776341A1 EP05796225A EP05796225A EP1776341A1 EP 1776341 A1 EP1776341 A1 EP 1776341A1 EP 05796225 A EP05796225 A EP 05796225A EP 05796225 A EP05796225 A EP 05796225A EP 1776341 A1 EP1776341 A1 EP 1776341A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
solvent
temperature
hai
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05796225A
Other languages
English (en)
French (fr)
Inventor
Pierre Jean Grossi
Raphaël SOLE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi SA
Original Assignee
Sanofi Aventis France
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.)
Filing date
Publication date
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Publication of EP1776341A1 publication Critical patent/EP1776341A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • 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
    • C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/30—Nitrogen atoms non-acylated
    • 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
    • C07D211/98—Nitrogen atom

Definitions

  • the subject of the present invention is a new process for preparing N-5. aminopiperidine of formula:
  • N-aminopiperidine (I) and its salts according to the present invention is characterized in that: a) a carbazate of formula:
  • R represents a (C 1 -C 8) alkyl group, a phenyl or a benzyl, with a pentyl 1,5-dihalide of the formula:
  • R represents a (C 1 -C 6) alkyl group, a phenyl or a benzyl in an acid medium or in a basic medium to obtain the expected N-aminopiperidine.
  • a salt of N-aminopiperidine (I) can be prepared by the action of a mineral or organic acid.
  • halogen atom is meant a bromine, chlorine or iodine atom.
  • Step b) is carried out either in an acid medium, for example in the presence of hydrochloric or hydrobromic acid, or in a basic medium, for example in the presence of potassium hydroxide or sodium hydroxide in a solvent such as water or ethanol and at a temperature between room temperature and the reflux temperature of the solvent.
  • an acid medium for example in the presence of hydrochloric or hydrobromic acid
  • a basic medium for example in the presence of potassium hydroxide or sodium hydroxide in a solvent such as water or ethanol and at a temperature between room temperature and the reflux temperature of the solvent.
  • step a) a compound of formula (II) in which R represents an ethyl radical is treated with a compound of formula (III) in which HaI represents a bromine atom, in acetonitrile, while refluxing the solvent.
  • step b) the compound of formula (IV) in which R represents an ethyl radical is treated with sodium hydroxide in water while heating at reflux of the solvent.
  • N-aminopiperidine salt such as hydrobromide, hydrochloride or oxalate is prepared.
  • N-aminopiperidine hydrobromide can be prepared in a solvent such as methyl-fert-butyl ether (MTBE).
  • a mixture of 565.3 g of ethyl carbazate in 373 ml of acetonitrile is prepared.
  • 415.4 g of 1,5-dibromopentane are poured onto the preceding mixture brought to reflux. Reflux is maintained for 3 hours.
  • Acetonitrile is removed by concentration in vacuo. The residue thus obtained is dissolved in a toluene / water mixture.
  • the aqueous phase is decanted and reextracted with toluene. Water and 36% HCl are added to the attached toluene phases.
  • the "rich" aqueous phase is washed 3 to 4 times with methyl-but-butyl ether (MTBE) to remove the neutral (impurities, diethyl carbazate, residual dibromopentane).
  • the acidic aqueous phase is basified with NaOH and then NaHCO3 in the presence of toluene.
  • the aqueous phase is reextracted with toluene.
  • the toluene phases are washed separately with water in order to deplete residual ethylcarbazate.
  • the toluene phases are concentrated to dryness.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP05796225A 2004-08-05 2005-08-02 Verfahren zur herstellung von n-aminopiperidin und seinen salzen Withdrawn EP1776341A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0408700A FR2874013B1 (fr) 2004-08-05 2004-08-05 Procede de preparation de la n-aminopiperidine et de ses sels
PCT/FR2005/002016 WO2006024778A1 (fr) 2004-08-05 2005-08-02 Procede de preparation de la n-aminopiperedine et de ses sels

Publications (1)

Publication Number Publication Date
EP1776341A1 true EP1776341A1 (de) 2007-04-25

Family

ID=34947045

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05796225A Withdrawn EP1776341A1 (de) 2004-08-05 2005-08-02 Verfahren zur herstellung von n-aminopiperidin und seinen salzen

Country Status (16)

Country Link
US (2) US20070173648A1 (de)
EP (1) EP1776341A1 (de)
JP (1) JP2008509114A (de)
KR (1) KR20070048765A (de)
CN (1) CN101001839A (de)
AR (1) AR050089A1 (de)
AU (1) AU2005279087A1 (de)
BR (1) BRPI0514076A (de)
CA (1) CA2576718A1 (de)
FR (1) FR2874013B1 (de)
IL (1) IL180870A0 (de)
MX (1) MX2007001140A (de)
RU (1) RU2373196C2 (de)
TW (1) TW200621713A (de)
UY (1) UY29045A1 (de)
WO (1) WO2006024778A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2864081B1 (fr) * 2003-12-17 2006-04-28 Isochem Sa Procede de synthese de derives de cycloalkyl-hydrazines exocycliques et de derives d'heterocycloalkyl-hydrazines exocycliques.

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE338609C (de) 1919-10-15 1921-06-22 Fritz Sommer Dr Verfahren zur Darstellung von Hydrazin und dessen Alkyl- oder Arylsubstitutionsprodukten
US3317607A (en) * 1959-07-30 1967-05-02 Fmc Corp Chemical reduction of nitrosamines
DE4138142C2 (de) * 1991-11-20 1996-04-25 Cassella Ag Verfahren zur Herstellung von 1-Amino-2,6-dimethylpiperidin
US5977360A (en) * 1996-12-27 1999-11-02 Japan Hydrazine Co., Ltd. Process for producing cyclic hydrazine derivatives, tetra-hydropyridazine and hexahydropyridazine
JP4118559B2 (ja) * 2001-12-19 2008-07-16 日本曹達株式会社 脂環式ヒドラジンの製造方法
JP2004137182A (ja) * 2002-10-17 2004-05-13 Nippon Soda Co Ltd Ｎ−アミノピペリジンの製造方法
JP2004137181A (ja) * 2002-10-17 2004-05-13 Nippon Soda Co Ltd Ｎ−アミノピペリジンの製造法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006024778A1 *

Also Published As

Publication number Publication date
US7951952B2 (en) 2011-05-31
TW200621713A (en) 2006-07-01
FR2874013B1 (fr) 2006-09-29
BRPI0514076A (pt) 2008-05-27
JP2008509114A (ja) 2008-03-27
UY29045A1 (es) 2006-03-31
RU2373196C2 (ru) 2009-11-20
US20070173648A1 (en) 2007-07-26
US20080306274A1 (en) 2008-12-11
IL180870A0 (en) 2009-02-11
AU2005279087A1 (en) 2006-03-09
CA2576718A1 (fr) 2006-03-09
KR20070048765A (ko) 2007-05-09
RU2007107806A (ru) 2008-09-10
FR2874013A1 (fr) 2006-02-10
CN101001839A (zh) 2007-07-18
AR050089A1 (es) 2006-09-27
WO2006024778A1 (fr) 2006-03-09
MX2007001140A (es) 2007-04-19

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