CA1088539A - Procede d'obtention de 5-(2-chlorobenzyl)-4,5,6,7- tetrahydrothieno ¬3,2-c| pyridine - Google Patents

Procede d'obtention de 5-(2-chlorobenzyl)-4,5,6,7- tetrahydrothieno ¬3,2-c| pyridine

Info

Publication number: CA1088539A
Authority: CA; Canada
Prior art keywords: chlorobenzyl; amine; pyridine; thienylethyl; tetrahydrothieno
Prior art date: 1977-01-27
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.): Expired

Application number

CA295,721A

Other languages

English (en)

Inventor

Giuseppe Quadro

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 SA

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.)

1977-01-27

Filing date

1978-01-26

Publication date

1980-10-28

1978-01-26 Application filed by Sanofi SA filed Critical Sanofi SA

1980-10-28 Application granted granted Critical

1980-10-28 Publication of CA1088539A publication Critical patent/CA1088539A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims abstract description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title abstract description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title abstract description 4
150000001412 amines Chemical class 0.000 claims abstract description 13
238000007363 ring formation reaction Methods 0.000 claims abstract description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000008346 aqueous phase Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
229960004279 formaldehyde Drugs 0.000 claims 1
235000019256 formaldehyde Nutrition 0.000 claims 1
KEOKHDKWKYGPGO-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-thiophen-2-ylethanamine Chemical compound ClC1=CC=CC=C1CNCCC1=CC=CS1 KEOKHDKWKYGPGO-UHFFFAOYSA-N 0.000 abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 7
150000001875 compounds Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
WUNFIVTVJXZDDJ-UHFFFAOYSA-N 1-thiophen-2-ylethanol Chemical compound CC(O)C1=CC=CS1 WUNFIVTVJXZDDJ-UHFFFAOYSA-N 0.000 description 2
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
238000006820 Bouveault-Blanc reduction reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PDGHMTYOQZXLPY-UHFFFAOYSA-N N-benzyl-N-chloro-2-thiophen-2-ylethanamine Chemical compound S1C(=CC=C1)CCN(Cl)CC1=CC=CC=C1 PDGHMTYOQZXLPY-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
-1 amine hydrochloride Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
FFVJAVUSCJCRPT-UHFFFAOYSA-N thiophen-2-yl acetate Chemical compound CC(=O)OC1=CC=CS1 FFVJAVUSCJCRPT-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA295,721A 1977-01-27 1978-01-26 Procede d'obtention de 5-(2-chlorobenzyl)-4,5,6,7- tetrahydrothieno ¬3,2-c| pyridine Expired CA1088539A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT41.002A.77		1977-01-27
IT41002/77A IT1082336B (it)	1977-01-27	1977-01-27	Processo per la preparazione della 5.2.clorobenzil.4 5 6 7.tetraidro tien 3 2.c.piridina

Publications (1)

Publication Number	Publication Date
CA1088539A true CA1088539A (fr)	1980-10-28

Family

ID=11249989

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA295,721A Expired CA1088539A (fr)	1977-01-27	1978-01-26	Procede d'obtention de 5-(2-chlorobenzyl)-4,5,6,7- tetrahydrothieno ¬3,2-c\| pyridine

Country Status (6)

Country	Link
JP (1)	JPS5395994A (fr)
CA (1)	CA1088539A (fr)
GR (1)	GR63080B (fr)
IT (1)	IT1082336B (fr)
NL (1)	NL7801004A (fr)
SE (1)	SE7800990L (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2508453A1 (fr) *	1981-06-30	1982-12-31	Sanofi Sa	Procede de preparation de derives des (thienyl-2)- et thienyl-3)-2 ethylamines et produits ainsi obtenus
EP0068979A1 (fr) *	1981-06-30	1983-01-05	Elf Sanofi	Procédé de préparation de dérivés des (thiényl-2)- et (thiényl-3)-2 éthylamines et produits ainsi obtenus
CN105601644A (zh) *	2015-12-31	2016-05-25	苏州弘森药业有限公司	一种合成盐酸噻氯匹定的新方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4906756A (en) *	1988-05-10	1990-03-06	Syntex (U.S.A.) Inc.	2-(2-nitrovinyl)thiophene reduction and synthesis of thieno[3,2-c]pyridine derivatives

1977
- 1977-01-27 IT IT41002/77A patent/IT1082336B/it active
1978
- 1978-01-26 SE SE7800990A patent/SE7800990L/xx unknown
- 1978-01-26 JP JP817978A patent/JPS5395994A/ja active Pending
- 1978-01-26 CA CA295,721A patent/CA1088539A/fr not_active Expired
- 1978-01-27 NL NL7801004A patent/NL7801004A/xx not_active Application Discontinuation
- 1978-01-27 GR GR55293A patent/GR63080B/el unknown

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2508453A1 (fr) *	1981-06-30	1982-12-31	Sanofi Sa	Procede de preparation de derives des (thienyl-2)- et thienyl-3)-2 ethylamines et produits ainsi obtenus
EP0068979A1 (fr) *	1981-06-30	1983-01-05	Elf Sanofi	Procédé de préparation de dérivés des (thiényl-2)- et (thiényl-3)-2 éthylamines et produits ainsi obtenus
EP0068978A1 (fr) *	1981-06-30	1983-01-05	Elf Sanofi	Procédé de préparation de dérivés des (thiényl-2)- et (thiényl-3)-2 éthylamines, et produits ainsi obtenus
CN105601644A (zh) *	2015-12-31	2016-05-25	苏州弘森药业有限公司	一种合成盐酸噻氯匹定的新方法

Also Published As

Publication number	Publication date
NL7801004A (nl)	1978-07-31
JPS5395994A (en)	1978-08-22
SE7800990L (sv)	1978-07-28
IT1082336B (it)	1985-05-21
GR63080B (en)	1979-08-08

Legal Events

Date	Code	Title	Description
1997-10-28	MKEX	Expiry

Publication	Publication Date	Title
KR100198503B1 (ko)	1999-06-15	테트라히드로티에노 (3,2-c) 피리딘의 n-페닐아세트 유도체 제조방법 및 그의 화학 중간 생성물
Peet et al.	1986	Mechanistic observations in the gewald syntheses of 2‐aminothiophenes
CA1088539A (fr)	1980-10-28	Procede d'obtention de 5-(2-chlorobenzyl)-4,5,6,7- tetrahydrothieno ¬3,2-c\| pyridine
Angier et al.	1950	Pteroic acid derivatives. VI. Unequivocal syntheses of some isomeric glutamic acid peptides
KR20050061503A (ko)	2005-06-22	티에노피롤 유도체의 제조 방법과 중간체
CA1055032A (fr)	1979-05-22	Procede pour la preparation de la thieno (3,2-c) pyridine et de la thieno (2,3-c) pyridine
CA2040518A1 (fr)	1991-10-17	Synthese d'analogues d'acide (s)-3-(thien-2-ylthio) butyrique
CA2040605A1 (fr)	1991-10-19	(s)-alkyl-3-(thien-2-ylthio)butyrate et analogues, ainsi que leur synthese
CA1060045A (fr)	1979-08-07	Les n-benzyl-2,2-dimethoxyacetamides
CN116410136B (zh)	2025-07-11	一种喹啉衍生物及其制备方法
US5516910A (en)	1996-05-14	N--2--chlorobenzyl--2--oxo and n--2--chlorobenzyl--2,2--dioxo--1,2,3--oxathiazolidine derivatives, their preparation and synthesis of thieno[3,2--c]pyridine derivatives therefrom
US2650226A (en)	1953-08-25	Furo and thieno quinaldines and process for making same
EP0522956B1 (fr)	1997-02-05	Préparation de 2-(2-thiényl)éthylamine, ainsi qu'une synthèse de dérivés de thiéno(3,2-c)pyridine correspondants
AU608768B2 (en)	1991-04-18	Aryloxycycloalkanolamines
US5545744A (en)	1996-08-13	Cyano naphthalene compounds
AU624100B2 (en)	1992-06-04	4-heteroaryl-1,3-benzodiazepines and 2-substituted-alpha- (heteroaryl) benzeneethanamines, a process for their preparation and their use as medicaments
SU468423A3 (ru)	1975-04-25	Способ получени 6-аза-3н-1,4-бензодиазепинов
RU2421453C9 (ru)	2011-11-20	Способ получения несимметричных 1,2-дитиенилзамещенных циклопентенов
AU650499B2 (en)	1994-06-23	The process for the preparation of enantiomerically pure thienopyran derivative
US4051127A (en)	1977-09-27	Preparation of benzodiazepine derivatives
SU1051092A1 (ru)	1983-10-30	Способ получени тиохиндолинов
CA2352520C (fr)	2007-10-02	Synthese de derives de tetrahydrothieno-[3,2-c]-pyridine
US4482711A (en)	1984-11-13	Process for the preparation of N,N-dimethyl-10-[1-aza-[2,2,2]-bicyclo-3-octyl]-10H-2-phenothiazine sulphonamide
CA1267905A (fr)	1990-04-17	Derive de thiophene
JPH02196784A (ja)	1990-08-03	２‐（２‐チェニル）‐エチルアミン誘導体の製造方法