CA1099719A - Procede de preparation de n-(1-benzylpiperid-4-yl)- benzamides - Google Patents

Procede de preparation de n-(1-benzylpiperid-4-yl)- benzamides

Info

Publication number: CA1099719A
Authority: CA; Canada
Prior art keywords: general formula; group; carbon atoms; benzylpiperid; process according
Prior art date: 1978-06-14
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

CA317,711A

Other languages

English (en)

Inventor

Jose Prieto Soto

Robert G. W. Spickett

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.)

Anphar SA

Original Assignee

Anphar 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.)

1978-06-14

Filing date

1978-12-11

Publication date

1981-04-21

1978-12-11 Application filed by Anphar SA filed Critical Anphar SA

1981-04-21 Application granted granted Critical

1981-04-21 Publication of CA1099719A publication Critical patent/CA1099719A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 31
230000008569 process Effects 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims description 6
229940054066 benzamide antipsychotics Drugs 0.000 title description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 15
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
-1 methylenedioxy group Chemical group 0.000 claims abstract description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 8
UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical class SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 5
239000003960 organic solvent Substances 0.000 claims abstract description 5
125000002252 acyl group Chemical group 0.000 claims abstract description 4
239000000460 chlorine Substances 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 claims abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 3
238000011065 in-situ storage Methods 0.000 claims abstract description 3
LDGORKJXEGHFBK-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 LDGORKJXEGHFBK-UHFFFAOYSA-N 0.000 claims abstract 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
239000000243 solution Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000003936 benzamides Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
238000001816 cooling Methods 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZJDAKFNBRCQNNT-UHFFFAOYSA-N 3-chlorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CC(Cl)=C1 ZJDAKFNBRCQNNT-UHFFFAOYSA-N 0.000 description 1
GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 1
BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 description 1
BRXXTVNYHGGBKP-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(N)=O BRXXTVNYHGGBKP-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000002804 dopamine agent Substances 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
229940005501 dopaminergic agent Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000010438 heat treatment Methods 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
150000003840 hydrochlorides Chemical class 0.000 description 1
229940049920 malate Drugs 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA317,711A 1978-06-14 1978-12-11 Procede de preparation de n-(1-benzylpiperid-4-yl)- benzamides Expired CA1099719A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES470772		1978-06-14
ES470772A ES470772A1 (es)	1978-06-14	1978-06-14	Procedimiento de preparacion de derivados de 4-aminopiperi- dina

Publications (1)

Publication Number	Publication Date
CA1099719A true CA1099719A (fr)	1981-04-21

Family

ID=8476283

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA317,711A Expired CA1099719A (fr)	1978-06-14	1978-12-11	Procede de preparation de n-(1-benzylpiperid-4-yl)- benzamides

Country Status (8)

Country	Link
JP (1)	JPS54163584A (fr)
AR (1)	AR224620A1 (fr)
BE (1)	BE872641A (fr)
CA (1)	CA1099719A (fr)
ES (1)	ES470772A1 (fr)
FR (1)	FR2428631A1 (fr)
IL (1)	IL56146A (fr)
NZ (1)	NZ189085A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5822232U (ja) *	1981-08-04	1983-02-10	相生精機株式会社	工作機械へのクランプパレツト交換装置

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1507463A (en) *	1975-03-10	1978-04-12	Gallardo Antonio Sa	N-(1-benzylpiperid-4-yl)-benzamides methods for their preparation and pharmaceutical compositions containing them

1978
- 1978-06-14 ES ES470772A patent/ES470772A1/es not_active Expired
- 1978-12-04 NZ NZ189085A patent/NZ189085A/xx unknown
- 1978-12-07 IL IL56146A patent/IL56146A/xx unknown
- 1978-12-08 FR FR7835285A patent/FR2428631A1/fr active Granted
- 1978-12-08 BE BE192227A patent/BE872641A/fr not_active IP Right Cessation
- 1978-12-11 CA CA317,711A patent/CA1099719A/fr not_active Expired
- 1978-12-11 JP JP15297578A patent/JPS54163584A/ja active Granted
- 1978-12-13 AR AR274784A patent/AR224620A1/es active

Also Published As

Publication number	Publication date
ES470772A1 (es)	1979-01-16
NZ189085A (en)	1981-04-24
JPS54163584A (en)	1979-12-26
FR2428631A1 (fr)	1980-01-11
IL56146A (en)	1982-07-30
AR224620A1 (es)	1981-12-30
BE872641A (fr)	1979-06-08
IL56146A0 (en)	1979-03-12
JPS612063B2 (fr)	1986-01-22
FR2428631B1 (fr)	1982-12-31

Legal Events

Date	Code	Title	Description
1998-04-21	MKEX	Expiry

Publication	Publication Date	Title
JP2015164968A (ja)	2015-09-17	Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの多形
CA2295800A1 (fr)	1999-01-21	Resolution d'amines
US3988341A (en)	1976-10-26	Esterification process
CA1099719A (fr)	1981-04-21	Procede de preparation de n-(1-benzylpiperid-4-yl)- benzamides
US4769465A (en)	1988-09-06	Process for the preparation of 2-(N-benzyl-N-methylamino)-ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and its hydrochloride salt
BRPI0608219A2 (pt)	2010-11-09	processo para preparar um grupo de amidina protegido, e, uso de um agente de ativação de tio-ceto
HUP0201980A2 (hu)	2004-03-01	Eljárás benzamidszármazék előállítására és az eljárás közbenső termékei
US3821238A (en)	1974-06-28	2-(b-aminoethylsulfonylamine)thiazole
EP1259509A1 (fr)	2002-11-27	Procede de preparation de 6-methyl-2-(4-methyl-phenyl)-imidazo 1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) et d'intermediaires
JP3207018B2 (ja)	2001-09-10	ベンジルコハク酸誘導体の製造方法およびその製造中間体
JPH01190655A (ja)	1989-07-31	飽和脂肪族α，ω−ジアミノモノカルボン酸のＮ，ωトリフルオロアセチル化方法
JP4463515B2 (ja)	2010-05-19	Ｌ−アンセリンの合成法
JPH0378384B2 (fr)	1991-12-13
JPS62155268A (ja)	1987-07-10	ナイザチジンの合成法
JPS6354700B2 (fr)	1988-10-28
CN1315781C (zh)	2007-05-16	制备4－氨基－1－萘酚醚类化合物的方法
Yamada et al.	1976	A Facile Method of Preparing l-α-Methyl DOPA (l-3-(3, 4-Dihydroxyphenyl)-2-methylalanine)
KR100288404B1 (ko)	2001-04-16	2-벤조티아졸릴 4-아미노-5-클로로-2-메톡시티오벤조에이트 및
JPS62167754A (ja)	1987-07-24	シアノメチルチオ酢酸類化合物の製造方法
US2966490A (en)	1960-12-27	Nu-[beta-(p-aminophenyl) ethyl]-4-phenyl-4-carboethoxypiperidine salts thereof and processes of preparing the same
US5326908A (en)	1994-07-05	Process for the preparation of asparagine
JP2625893B2 (ja)	1997-07-02	光学活性アラニンエステル誘導体の選択的製造法
CA1055951A (fr)	1979-06-05	Procede pour la preparation de la 1-ethyl-2,2'-methoxy-5'-sulfonamidobenzoylaminomethylpyrrolidine et de ses sels
US2517496A (en)	1950-08-01	Preparation of symmetrical monoaminodihydroxytoluene
KR790001576B1 (ko)	1979-11-05	1, 4-치환-4-(3, 4-메틸렌디옥시페닐)-피페리딘의 제조방법