SE8401554L - PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE - Google Patents

PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE

Info

Publication number
SE8401554L
SE8401554L SE8401554A SE8401554A SE8401554L SE 8401554 L SE8401554 L SE 8401554L SE 8401554 A SE8401554 A SE 8401554A SE 8401554 A SE8401554 A SE 8401554A SE 8401554 L SE8401554 L SE 8401554L
Authority
SE
Sweden
Prior art keywords
product
reacting
bis
flecainide
alpha
Prior art date
Application number
SE8401554A
Other languages
Swedish (sv)
Other versions
SE447993B (en
SE8401554D0 (en
Inventor
C M Leir
Original Assignee
Riker Laboratories 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.)
Filing date
Publication date
Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc
Publication of SE8401554L publication Critical patent/SE8401554L/en
Publication of SE8401554D0 publication Critical patent/SE8401554D0/en
Publication of SE447993B publication Critical patent/SE447993B/en

Links

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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Abstract

A process for preparing flecainide comprises reacting para-dibromo- benzene or para-dihydroxybenzene with a compound of formula CF3CH2O- A wherein A is -SO2CF3 or an alkali metal, acetylating the resulting 1,4- bis(trifluoroethoxy) benzene to give the bis (trifluoroethoxy) acetophenone in the presence of a Lewis acid catalyst, then either chlorinating the acetylated product, adding a buffering base and further chlorinating to form the corresponding alpha , alpha , alpha -trichloroacetophenone or reacting the acetylated acetophenone with hypochlorite to form the corresponding benzoic acid and reacting the acid with an inorganic acid chloride to provide the corresponding acid chloride, and then reacting the product of either of the latter pair of steps with 2-amino-methyl-piperidine to form the flecainide product in one step or with two 2-amino-methyl- pyridine followed by reduction to form the flecainide product in two steps. Individual reaction steps in the above scheme are presented as being novel per se, as are some of the intermediate compounds formed.
SE8401554A 1979-03-19 1984-03-21 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE SE447993B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2133279A 1979-03-19 1979-03-19
US2133179A 1979-03-19 1979-03-19

Publications (3)

Publication Number Publication Date
SE8401554L true SE8401554L (en) 1984-03-21
SE8401554D0 SE8401554D0 (en) 1984-03-21
SE447993B SE447993B (en) 1987-01-12

Family

ID=26694559

Family Applications (5)

Application Number Title Priority Date Filing Date
SE8002003A SE447992B (en) 1979-03-19 1980-03-14 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8401555A SE463260B (en) 1979-03-19 1984-03-21 acetophenone
SE8401554A SE447993B (en) 1979-03-19 1984-03-21 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8901533A SE463419B (en) 1979-03-19 1989-04-27 acetophenone
SE8901532A SE463418B (en) 1979-03-19 1989-04-27 acetophenone

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SE8002003A SE447992B (en) 1979-03-19 1980-03-14 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8401555A SE463260B (en) 1979-03-19 1984-03-21 acetophenone

Family Applications After (2)

Application Number Title Priority Date Filing Date
SE8901533A SE463419B (en) 1979-03-19 1989-04-27 acetophenone
SE8901532A SE463418B (en) 1979-03-19 1989-04-27 acetophenone

Country Status (14)

Country Link
JP (8) JPH01125341A (en)
CA (1) CA1137486A (en)
CH (1) CH643829A5 (en)
DE (1) DE3010195A1 (en)
DK (3) DK167062B1 (en)
ES (1) ES8104227A1 (en)
FR (7) FR2454438A1 (en)
GB (2) GB2045760B (en)
IE (1) IE49558B1 (en)
IL (1) IL59623A (en)
IT (1) IT1195262B (en)
NL (1) NL191486C (en)
PT (1) PT70967A (en)
SE (5) SE447992B (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2519980A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE SULFONYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
FR2519974A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE ACYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
FR2519975A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR PREPARING TRIFLUOROMETHOXY OR TRIFLUOROMETHYLTHIOPHENYLCETONES
FR2519979A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF TRIFLUOROMETHOXY OR TRIFLUOROMETHYLTHIOPHENYLSULFONES
FR2525588A1 (en) * 1982-04-22 1983-10-28 Rhone Poulenc Spec Chim PROCESS FOR PREPARING PHENYLCETONES FROM HALOGENO OR TRIHALOGENOMETHYLBENZENES AND ALIPHATIC OR AROMATIC TRIHALOGENOMETHYL COMPOUNDS
EP0175188A1 (en) * 1984-09-11 1986-03-26 Nihon Tokushu Noyaku Seizo K.K. Carbamoylimidazole derivatives
US4675448A (en) * 1985-02-13 1987-06-23 Ethyl Corporation Chlorination process
FR2579594B1 (en) * 1985-03-29 1987-06-05 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF TRIFLUOROETHOXY OR TRIFLUOROETHYLTHIOBENZENES
FR2579591B1 (en) * 1985-03-29 1988-10-14 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF PENTAFLUOROETHOXY AND PENTAFLUOROETHYLTHIOBENZENIQUE DERIVATIVES
EP0242847B1 (en) * 1986-04-25 1993-06-02 Abbott Laboratories Tracers for use in flecainide fluorescence polarization immunoassay
NZ219913A (en) * 1986-04-25 1990-08-28 Riker Laboratories Inc Various flecainide derivatives and antibodies raised thereto
DE3644798A1 (en) * 1986-12-31 1988-07-14 Hoechst Ag NEW NITROHALOALCOXYBENZOLS, METHOD FOR THEIR PRODUCTION AND THEIR USE
FR2640262B1 (en) * 1988-12-14 1991-05-31 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF TRIFLUOROETHOXYLATED ARYLIC KETONES
IL121288A (en) 1997-07-11 2000-10-31 Finetech Ltd Process and a novel intermediate for the preparation of flecainide
US6316627B1 (en) 1997-04-21 2001-11-13 Fine Tech Ltd. Process for the preparation of flecainide
IL120715A (en) * 1997-04-21 2000-07-16 Finetech Ltd Process for the preparation of (2,2,2,-trifluoroethoxy)benzoic acids
US7196197B2 (en) 2003-09-17 2007-03-27 Apotex Pharmachem Inc. Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof
JP4894226B2 (en) * 2005-10-31 2012-03-14 Ｄｉｃ株式会社 Method for producing fluorine-containing liquid crystal compound having hydroquinone skeleton

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539642A (en) * 1967-07-19 1970-11-10 Geigy Chem Corp 2-phenyl-2-(1-naphthyl)acetamides
US3772304A (en) * 1969-10-30 1973-11-13 Hoffmann La Roche 4-hydroxy-isoquinolines and processes for their preparation
US3655728A (en) 1970-07-22 1972-04-11 Riker Laboratories Inc N-(2 - dialkylaminoalkylene)-esters of fluoroalkoxy-substituted aryl carboxylic acid and salts thereof
US3719687A (en) * 1970-07-22 1973-03-06 Riker Laboratories Inc N-(2-dialkylaminoalkylene)amides of 1,1-dihydroperfluoroalkoxy-substituted aryl acids and salts thereof
US3967949A (en) * 1973-06-18 1976-07-06 Eli Lilly And Company Fluoroalkoxyphenyl-substituted nitrogen heterocycles as plant stunting agents
US4169108A (en) * 1973-08-16 1979-09-25 Sterling Drug Inc. 5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols
US4005209A (en) * 1974-04-01 1977-01-25 Riker Laboratories, Inc. Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides
US3900481A (en) * 1974-04-01 1975-08-19 Riker Laboratories Inc Derivatives of pyrrolidine and piperidine
US4013670A (en) * 1974-04-01 1977-03-22 Riker Laboratories, Inc. Derivatives of pyrrolidine and piperidine
IL49803A (en) * 1975-06-28 1979-11-30 Fisons Ltd Preparation of pyrogallol
DE2616478C2 (en) * 1976-04-14 1986-05-22 Brickl, Rolf, Dr., 7951 Warthausen Medicines, biocides and cosmetics containing fluoroacylresorcins
JPS6023656B2 (en) * 1976-09-02 1985-06-08 川研フアインケミカル株式会社 Method for producing alkoxy aromatic compounds
US4071524A (en) * 1976-11-08 1978-01-31 Riker Laboratories, Inc. Derivatives of urea
US4097481A (en) * 1976-11-08 1978-06-27 Riker Laboratories, Inc. Tertiary amide derivatives of pyrrolidine and piperidine

Also Published As

Publication number Publication date
DK79891D0 (en) 1991-04-30
NL8001551A (en) 1980-09-23
GB2097000B (en) 1983-11-30
FR2468576A1 (en) 1981-05-08
NL191486C (en) 1995-08-04
GB2045760B (en) 1983-05-11
FR2468591B1 (en) 1983-07-22
JPH01125341A (en) 1989-05-17
IL59623A0 (en) 1980-06-30
NL191486B (en) 1995-04-03
SE8901532D0 (en) 1989-04-27
DK122290A (en) 1990-05-17
FR2468576B1 (en) 1983-01-21
SE8002003L (en) 1980-09-20
SE447992B (en) 1987-01-12
FR2468591A1 (en) 1981-05-08
JPH0251906B2 (en) 1990-11-08
JPH0372212B2 (en) 1991-11-18
DK167062B1 (en) 1993-08-23
DK79891A (en) 1991-04-30
FR2468569A1 (en) 1981-05-08
SE447993B (en) 1987-01-12
FR2454438B1 (en) 1982-07-23
SE8901532L (en) 1989-04-27
JPH01125344A (en) 1989-05-17
CH643829A5 (en) 1984-06-29
IT8020746A0 (en) 1980-03-18
FR2468570B1 (en) 1983-03-11
ES489629A0 (en) 1981-04-01
SE8401555D0 (en) 1984-03-21
CA1137486A (en) 1982-12-14
DE3010195A1 (en) 1980-10-02
IL59623A (en) 1983-07-31
JPH01125343A (en) 1989-05-17
DK122290D0 (en) 1990-05-17
JPH01104044A (en) 1989-04-21
JPH022869B2 (en) 1990-01-19
SE463260B (en) 1990-10-29
DK164857B (en) 1992-08-31
FR2468570A1 (en) 1981-05-08
FR2454438A1 (en) 1980-11-14
IE49558B1 (en) 1985-10-30
FR2468571B1 (en) 1983-03-11
ES8104227A1 (en) 1981-04-01
JPH01125339A (en) 1989-05-17
JPH0251908B2 (en) 1990-11-08
JPH01125342A (en) 1989-05-17
SE8901533L (en) 1989-04-27
SE463419B (en) 1990-11-19
GB2097000A (en) 1982-10-27
DK164857C (en) 1993-01-18
IT1195262B (en) 1988-10-12
JPH022870B2 (en) 1990-01-19
FR2468569B1 (en) 1983-03-11
DK112180A (en) 1980-09-20
FR2468590B1 (en) 1983-09-23
SE463418B (en) 1990-11-19
JPH0149695B2 (en) 1989-10-25
FR2468590A1 (en) 1981-05-08
JPH01104043A (en) 1989-04-21
GB2045760A (en) 1980-11-05
SE8401554D0 (en) 1984-03-21
SE8901533D0 (en) 1989-04-27
FR2468571A1 (en) 1981-05-08
JPH01104045A (en) 1989-04-21
PT70967A (en) 1980-04-01
JPH0251907B2 (en) 1990-11-08
SE8401555L (en) 1984-03-21
DE3010195C2 (en) 1990-10-25
IE800549L (en) 1980-09-19
JPH0339498B2 (en) 1991-06-14

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