CA1072093A - Production de derives basiques de triphenylalcene - Google Patents

Production de derives basiques de triphenylalcene

Info

Publication number: CA1072093A
Authority: CA; Canada
Prior art keywords: general formula; isomers; denotes; dimethylamino; salts
Prior art date: 1976-02-05
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

CA271,083A

Other languages

English (en)

Inventor

Tibor Horvath

Gizella Abraham

Geza Schneider

Lajos Toldy

Odon Feher

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.)

Egyt Gyogyszervegyeszeti Gyar

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1976-02-05

Filing date

1977-02-04

Publication date

1980-02-19

1977-02-04 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1980-02-19 Application granted granted Critical

1980-02-19 Publication of CA1072093A publication Critical patent/CA1072093A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title claims abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 18
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 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 11
229910052708 sodium Inorganic materials 0.000 claims abstract description 11
239000011734 sodium Substances 0.000 claims abstract description 11
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001502 aryl halides Chemical class 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
150000001340 alkali metals Chemical class 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
239000000243 solution Substances 0.000 claims description 12
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 5
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
150000003840 hydrochlorides Chemical class 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
239000011260 aqueous acid Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
230000001419 dependent effect Effects 0.000 abstract description 3
206010028980 Neoplasm Diseases 0.000 abstract description 2
229940046836 anti-estrogen Drugs 0.000 abstract description 2
230000001833 anti-estrogenic effect Effects 0.000 abstract description 2
201000011510 cancer Diseases 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
239000000328 estrogen antagonist Substances 0.000 abstract description 2
125000005842 heteroatom Chemical group 0.000 abstract description 2
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
229940088597 hormone Drugs 0.000 abstract description 2
239000005556 hormone Substances 0.000 abstract description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 6
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
230000007935 neutral effect Effects 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
-1 phenethylphenyl halides Chemical class 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960001603 tamoxifen Drugs 0.000 description 3
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000002301 combined effect Effects 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
150000002221 fluorine Chemical class 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
KDKKRJMQCQNZDY-UHFFFAOYSA-N 1-(1,2-diphenylbut-1-enyl)-4-fluorobenzene Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 KDKKRJMQCQNZDY-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
229940085033 nolvadex Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA271,083A 1976-02-05 1977-02-04 Production de derives basiques de triphenylalcene Expired CA1072093A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU76GO00001327A HU172948B (hu)	1976-02-05	1976-02-05	Sposob poluchenija osnovnykh proizvodnykh trifenil-alkenov

Publications (1)

Publication Number	Publication Date
CA1072093A true CA1072093A (fr)	1980-02-19

Family

ID=10996801

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA271,083A Expired CA1072093A (fr)	1976-02-05	1977-02-04	Production de derives basiques de triphenylalcene

Country Status (9)

Country	Link
JP (1)	JPS5921861B2 (fr)
AT (1)	AT347929B (fr)
CA (1)	CA1072093A (fr)
CH (1)	CH624923A5 (fr)
CS (1)	CS192475B2 (fr)
HU (1)	HU172948B (fr)
PL (1)	PL109347B1 (fr)
SU (1)	SU612622A3 (fr)
YU (1)	YU40811B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI67538C (fi) *	1982-05-27	1985-04-10	Farmos Oy	Foerfarande foer framstaellning av (z)-1,2-difenyl-1-(4-(2-(n n-dimetylamino)etoxi)fenyl)-1-buten
DE3462398D1 (en) *	1983-05-24	1987-04-02	Bristol Myers Co	Process for the conversion of the e isomer of 1,2-diphenyl-1-(4-(2-dimethylaminoethoxy)-phenyl)-1-butene to tamoxifen hcl
KR100303634B1 (ko)	1992-10-27	2001-11-22	다께다 가즈히꼬	자기면역질환치료약
JP4940429B2 (ja) *	2006-09-19	2012-05-30	国立大学法人岡山大学	トリアリールエチルエテン誘導体の製造方法

1976
- 1976-02-05 HU HU76GO00001327A patent/HU172948B/hu unknown
1977
- 1977-01-26 YU YU20577A patent/YU40811B/xx unknown
- 1977-02-01 AT AT59677A patent/AT347929B/de not_active IP Right Cessation
- 1977-02-02 SU SU772447049A patent/SU612622A3/ru active
- 1977-02-04 CA CA271,083A patent/CA1072093A/fr not_active Expired
- 1977-02-04 CS CS74577A patent/CS192475B2/cs unknown
- 1977-02-04 PL PL19582477A patent/PL109347B1/pl unknown
- 1977-02-04 JP JP1084677A patent/JPS5921861B2/ja not_active Expired
- 1977-02-04 CH CH135977A patent/CH624923A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
PL109347B1 (en)	1980-05-31
SU612622A3 (ru)	1978-06-25
CH624923A5 (en)	1981-08-31
HU172948B (hu)	1979-01-28
JPS5921861B2 (ja)	1984-05-22
JPS52122351A (en)	1977-10-14
AT347929B (de)	1979-01-25
ATA59677A (de)	1978-06-15
CS192475B2 (en)	1979-08-31
YU40811B (en)	1986-06-30
YU20577A (en)	1982-06-30

Legal Events

Date	Code	Title	Description
1997-02-19	MKEX	Expiry

Publication	Publication Date	Title
SU1005655A3 (ru)	1983-03-15	Способ получени 3-арилокси-3-фенилпропиламинов или их солей
CA1155115A (fr)	1983-10-11	Ethers basiques, procede de preparation et composes pharmaceutiques les contenant
EP0529842B1 (fr)	1996-04-24	Production de fluoxétine et intermédiaires
Lazbin et al.	1986	Direct conversion of aliphatic carboxamides to alkylammonium tosylates with [hydroxy (tosyloxy) iodo] benzene
JPS5850984B2 (ja)	1983-11-14	チカンジフエニルエ−テルルイ
CA1072093A (fr)	1980-02-19	Production de derives basiques de triphenylalcene
Barluenga et al.	1982	. beta.-Substituted organolithium compounds. Reaction with alkyl halides, dimethyl disulfide, and imines
US2774770A (en)	1956-12-18	Sulfur-containing amines
NZ219069A (en)	1990-11-27	Amine derivatives useful as a systemic antimycotic or an agrofungicide
CN104591959A (zh)	2015-05-06	一种二苯乙烯类化合物的制备方法
CA1062255A (fr)	1979-09-11	Composes macrocycliques et melanges qui en sont faits
US2574150A (en)	1951-11-06	Acenaphthenyl amino alcohols
EP0031218B1 (fr)	1983-05-11	Composé 2-amino-trifluorométhyl-halogénopyridine et procédé pour sa préparation
CA2137761C (fr)	1998-05-12	Methode de preparation de derives de chlorure de propargylammonium
CN115124434A (zh)	2022-09-30	一种亲核氟化试剂及其合成工艺、应用
US2881172A (en)	1959-04-07	Chemical compounds
US4507499A (en)	1985-03-26	N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide and method for producing trimethobenzamide chlorohydrate
US2763687A (en)	1956-09-18	Fluorene derivatives
US2854483A (en)	1958-09-30	Bronchodilator compounds
CA1041098A (fr)	1978-10-24	Derives de ((napht-1-yl-oxy)-3 propyl)-1 piperozine
US2772311A (en)	1956-11-27	Hydrogenating ketiminomagnesium halide intermediates with lithium aluminum hydride to produce amines
CA1068289A (fr)	1979-12-18	Preparation de derives du 2-aminoindane
US2683715A (en)	1954-07-13	I-tertiary amino-i-alkyl-piperidines
JPS62108867A (ja)	1987-05-20	イミダゾリル−メタン誘導体の製造方法
US4188343A (en)	1980-02-12	Process for preparing anthranylaldehyde derivatives