CA1058615A - Process for benz(f)-2,5-oxazocines - Google Patents
Process for benz(f)-2,5-oxazocinesInfo
- Publication number
- CA1058615A CA1058615A CA245,538A CA245538A CA1058615A CA 1058615 A CA1058615 A CA 1058615A CA 245538 A CA245538 A CA 245538A CA 1058615 A CA1058615 A CA 1058615A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- zero
- phenyl
- solvent
- reaction
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- HHDZPYDYAHWNKQ-UHFFFAOYSA-N 3h-4,1-benzoxazocine Chemical class N1=CCOC=CC2=CC=CC=C21 HHDZPYDYAHWNKQ-UHFFFAOYSA-N 0.000 title 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 10
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229960001701 chloroform Drugs 0.000 description 7
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- -1 hydrogen halides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SFVYUAJWNYVQDB-UHFFFAOYSA-N 2h-1,2-benzoxazocine Chemical compound O1NC=CC=CC2=CC=CC=C21 SFVYUAJWNYVQDB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LUQBVWFXYZAHCZ-UHFFFAOYSA-N 5-methyl-1-phenyl-2,4,5,6-tetrahydro-1h-3,4-benzoxazocine Chemical compound C1ONC(C)CC2=CC=CC=C2C1C1=CC=CC=C1 LUQBVWFXYZAHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/22—Eight-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/556,315 US3978085A (en) | 1975-03-07 | 1975-03-07 | Process for benz[f]-2,5-oxazocines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058615A true CA1058615A (en) | 1979-07-17 |
Family
ID=24220811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,538A Expired CA1058615A (en) | 1975-03-07 | 1976-02-11 | Process for benz(f)-2,5-oxazocines |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3978085A (en, 2012) |
| JP (1) | JPS51113889A (en, 2012) |
| AR (1) | AR211856A1 (en, 2012) |
| AT (1) | AT351548B (en, 2012) |
| AU (1) | AU510010B2 (en, 2012) |
| BE (1) | BE839252A (en, 2012) |
| CA (1) | CA1058615A (en, 2012) |
| CH (1) | CH616416A5 (en, 2012) |
| CS (1) | CS186732B2 (en, 2012) |
| DE (1) | DE2609015C2 (en, 2012) |
| DK (1) | DK142283B (en, 2012) |
| ES (1) | ES445556A1 (en, 2012) |
| FI (1) | FI61310C (en, 2012) |
| FR (1) | FR2303007A1 (en, 2012) |
| GB (1) | GB1545872A (en, 2012) |
| IL (1) | IL49160A (en, 2012) |
| MX (1) | MX3577E (en, 2012) |
| NL (1) | NL7601985A (en, 2012) |
| NO (1) | NO145138C (en, 2012) |
| PH (1) | PH12176A (en, 2012) |
| SE (1) | SE427929B (en, 2012) |
| ZA (1) | ZA76183B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208349A (en) * | 1978-07-27 | 1980-06-17 | Riker Laboratories, Inc. | Process for the preparation of 2-[N-(2-hydroxyethyl)-N-lower alkylaminomethyl]benzhydrols |
| US4626522A (en) * | 1980-01-17 | 1986-12-02 | John Wyeth & Brother Limited | Benzoxazocines intermediates |
| US4318909A (en) * | 1980-01-17 | 1982-03-09 | John Wyeth & Brother Limited | Benzoxazocines |
| US20060019940A1 (en) * | 2002-12-20 | 2006-01-26 | Baxter Andrew D | Novel benzoxazocines and their therapeutic use |
| BR0317467A (pt) * | 2002-12-20 | 2005-11-16 | Arakis Ltd | Benzoxazocinas e seu uso como inibidores de reassimilação de monoaminas |
| AU2005235786A1 (en) * | 2004-04-21 | 2005-11-03 | Sosei R&D Ltd. | Benzoxazocines and their therapeutic use as monoamine reuptake inhibitors |
| CN102363610A (zh) * | 2011-11-01 | 2012-02-29 | 安徽万和制药有限公司 | 一种合成盐酸奈福泮的新方法 |
| CN107556263A (zh) * | 2016-06-30 | 2018-01-09 | 康普药业股份有限公司 | 一种盐酸奈福泮的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA863349A (en) * | 1971-02-09 | Riker Laboratories, Inc. | Heterocyclic compounds |
-
1975
- 1975-03-07 US US05/556,315 patent/US3978085A/en not_active Expired - Lifetime
-
1976
- 1976-01-13 ZA ZA00760183A patent/ZA76183B/xx unknown
- 1976-02-11 CA CA245,538A patent/CA1058615A/en not_active Expired
- 1976-02-26 NL NL7601985A patent/NL7601985A/xx not_active Application Discontinuation
- 1976-02-26 DK DK83376AA patent/DK142283B/da unknown
- 1976-02-26 NO NO760656A patent/NO145138C/no unknown
- 1976-02-26 SE SE7602449A patent/SE427929B/xx unknown
- 1976-02-26 ES ES445556A patent/ES445556A1/es not_active Expired
- 1976-03-01 CH CH252976A patent/CH616416A5/de not_active IP Right Cessation
- 1976-03-04 DE DE2609015A patent/DE2609015C2/de not_active Expired
- 1976-03-05 JP JP51024042A patent/JPS51113889A/ja active Pending
- 1976-03-05 PH PH18179A patent/PH12176A/en unknown
- 1976-03-05 IL IL49160A patent/IL49160A/xx unknown
- 1976-03-05 BE BE164904A patent/BE839252A/xx not_active IP Right Cessation
- 1976-03-05 FI FI760573A patent/FI61310C/fi not_active IP Right Cessation
- 1976-03-05 AR AR262450A patent/AR211856A1/es active
- 1976-03-05 AU AU11705/76A patent/AU510010B2/en not_active Expired
- 1976-03-05 FR FR7606418A patent/FR2303007A1/fr active Granted
- 1976-03-05 CS CS7600001466A patent/CS186732B2/cs unknown
- 1976-03-05 MX MX7645U patent/MX3577E/es unknown
- 1976-03-05 AT AT164476A patent/AT351548B/de not_active IP Right Cessation
- 1976-03-08 GB GB9209/76A patent/GB1545872A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA164476A (de) | 1979-01-15 |
| NO145138C (no) | 1982-01-20 |
| FR2303007A1 (fr) | 1976-10-01 |
| FI61310B (fi) | 1982-03-31 |
| CS186732B2 (en) | 1978-12-29 |
| JPS51113889A (en) | 1976-10-07 |
| IL49160A (en) | 1979-01-31 |
| NO145138B (no) | 1981-10-12 |
| AU510010B2 (en) | 1980-06-05 |
| DE2609015C2 (de) | 1986-05-07 |
| CH616416A5 (en, 2012) | 1980-03-31 |
| US3978085A (en) | 1976-08-31 |
| DK142283B (da) | 1980-10-06 |
| FR2303007B1 (en, 2012) | 1980-02-08 |
| AU1170576A (en) | 1977-09-08 |
| SE7602449L (sv) | 1976-09-08 |
| ZA76183B (en) | 1976-12-29 |
| DK83376A (en, 2012) | 1976-09-08 |
| AR211856A1 (es) | 1978-03-31 |
| MX3577E (es) | 1981-03-19 |
| FI61310C (fi) | 1982-07-12 |
| SE427929B (sv) | 1983-05-24 |
| BE839252A (fr) | 1976-09-06 |
| NO760656L (en, 2012) | 1976-09-08 |
| DK142283C (en, 2012) | 1981-03-02 |
| GB1545872A (en) | 1979-05-16 |
| PH12176A (en) | 1978-11-21 |
| NL7601985A (nl) | 1976-09-09 |
| AT351548B (de) | 1979-07-25 |
| DE2609015A1 (de) | 1976-09-16 |
| FI760573A7 (en, 2012) | 1976-09-08 |
| IL49160A0 (en) | 1976-05-31 |
| ES445556A1 (es) | 1977-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1058615A (en) | Process for benz(f)-2,5-oxazocines | |
| JP3067878B2 (ja) | ２−（２’，４’−ジヒドロキシフェニル）−４，６−ジアリール−ｓ−トリアジンの製造方法 | |
| NO853255L (no) | Fremgangsmaate for fremstilling av 6-klor-n-metyl-2,3,4,5-tetrahydro-1h-3-benzazepin. | |
| US5034541A (en) | Method of preparing 1-phenyl-1-diethylaminocarbonyl-2-phthalimidomethyl-cyclopropane-z | |
| KR860001547B1 (ko) | d-2-(6-메톡시-2-나프틸)-프로피온산의 제조방법 | |
| JPH09509929A (ja) | エポキシドの合成方法 | |
| JPH0248548B2 (en, 2012) | ||
| JPH10298130A (ja) | トリクロロイソシアヌル酸を用いた置換アルケンの塩素化 | |
| CA1128952A (en) | Process for the preparation of a carbazole derivative | |
| JPS6054948B2 (ja) | α，β↓−不飽和環状脂肪族ケトキシムから芳香族アミンを製造する方法 | |
| US3888871A (en) | Process for the preparation of 4-chloro-2-hydroxybenzothiazole | |
| JPH0617342B2 (ja) | 光学活性β−アミノアルコ−ルの製造方法 | |
| US4677228A (en) | Chemical process | |
| JPH0240655B2 (en, 2012) | ||
| EP1281708B1 (en) | Process for the preparation of 5-Formylphthalide | |
| SU534183A3 (ru) | Способ получени производных бензоциклогептаоксазолона | |
| US4288635A (en) | Method for the preparation of (E)-4-bromo-2-methylbut-2-en-1-al | |
| JP3084577B2 (ja) | 光学活性なアトロラクチン酸の製造方法および製造の中間体 | |
| JPH0881456A (ja) | １，１，３，３−テトラクロロ−１，３−ジヒドロイソベンゾフラン誘導体の製造法 | |
| JPS6287599A (ja) | エリスロマイシン類のオキシム誘導体の製造法 | |
| JPS61172846A (ja) | （±）−２−クロロプロピオン酸の光学分割法 | |
| US1930753A (en) | Chlorination of cresidine | |
| NO831362L (no) | Fremgangsmaate ved fremstilling av o-nitrobenzaldehyd. | |
| US3422115A (en) | Process for producing 5-methylisoxazole | |
| JPH026340B2 (en, 2012) |