NZ206991A - N-(3-(phthal-1-imido)propyl)-o-benzamidodiphenylhlamines - Google Patents
N-(3-(phthal-1-imido)propyl)-o-benzamidodiphenylhlaminesInfo
- Publication number
- NZ206991A NZ206991A NZ20699181A NZ20699181A NZ206991A NZ 206991 A NZ206991 A NZ 206991A NZ 20699181 A NZ20699181 A NZ 20699181A NZ 20699181 A NZ20699181 A NZ 20699181A NZ 206991 A NZ206991 A NZ 206991A
- Authority
- NZ
- New Zealand
- Prior art keywords
- propyl
- phthalimido
- benzamidodiphenylhlamines
- phthal
- imido
- Prior art date
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
New Zealand Paient Spedficaiion for Paient Number £06991
20699 1
Priority Date(s): 8'.
Complete Specification Filed: f7.~, Urf&l. Class:
Publication Date: ...
P.O. Journal, No: iBftQ
Under the provision of R$gus,
lation 23 (I) the J
-d> j
Specification bas been ante-date4!
.../3. //osl£.n\.&&As 19£7 ■
Patents Form No. 5
NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION
y
JANifg4 \
S I V t'
PHTHALIMIDOPROPYL-BENZAMIDO-DIPHENYLAMINES WE, A.H. ROBINS COMPANY, INC. a corporation organised under the laws of the State of Virginia, U.S.A. of 1407 Cummings Drive, Richmond, Virginia 23220, U.S.A. hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:-
«2.£><"> 9 ^ I
This invention relates to N-[3-(1-phthalimido)-propyl]-o-benzamido-diphenylamines. Such compounds can be used to produce certain 5-aminopropyl-dibenzodiazepines which are claimed in N.Z. Patent Specification No. 206990 and, other such dibenzodiazepines, the use of which is described and claimed in N.Z. Patent Specification No. 198986 from which this specification and No. 206990 have been divided.
The compounds of this invention have the formula:
°^NnC'° IIb wherein X is selected from the group consisting of hydrogen, chlorine, bromine and fluorine.
The benzamido compounds of this invention are prepared by a modification of the procedure of British Patent 907,646. Ortho-nitro-diphenylamine is first reductively alkylated with a solution of ■ohloropropyl dimethylomiwe eg 3-(1-phthalimido)-l-chloropropane and following this the nitro moiety is reduced with hydrogen over palladium on carbon to
206991
give the corresponding ortho amino compound. The amino
«. .
radical in the ortho position is then reacted with thA benzoyl halide or a substituted benzoyl halide. The equation is as follows:
02N
VI
I 1) NaH
I 2) Cl-(CH2)3Q
n„ m
Q = 1-phthalimido.
20699 1
- 4 -Preparation 1 N-(3-Dimethylaminopropyl)-o-benzamidodiphenylamine.
To a solution of 15.5 g (0.075 mole) of N-(3-dimethylamino-propyl)-o-aminodiphenylamine in 100 ml of pyridine cooled to about 5°C. under nitrogen atmosphere was added 17.8 g (0.063 mole) of benzoyl chloride. A small amount of benzene was used to wash the remaining benzoyl chloride into the reaction vessel. The mixture was stirred for 1 hr and the vessel stoppered and placed in the refrigerator over the weekend. The solvent was then evaporated under reduced pressure. The residual oil was dissolved in 100 ml of methylene chloride and the solution washed once with 150 ml of 3 N sodium hydroxide and three times with 250 ml of water. The methylene chloride layer was dried over magnesium sulfate and evaporated under reduced pressure. Residual pyridine was then removed under high vacuum (0.2 mm Hg) overnight. Weight of the residual oil, the free base, was 24.9 g.
Oxalate Salt - To a hot solution of 4.0 g of the free base in isopropyl alcohol was added 1.35 g (0.0107 mole) of oxalic acid dihydrate. The precipitated oxalate salt of the title compound weighed 3.5 g and melted at 162-5°C. The salt after drying 1 hr at 97-98°C. (refluxing propyl alcohol) and overnight at room temperature all at 0.1 mm Hg., analyzed as follows:
Analysis: Calculated for C26H29N3°5: c'67*37* H,6.31y N,9.06 Found : C,67.42; H,6.35; N,9.01
206991
Preparation 2 N-[3-(1-Phthalimido)propyl]-o-aminodiphenylamine. o-Nitrodiphenylamine is reacted with sodium hydride and 3-(1-phthalimido)-l-chloropropane to give N-3-(l-phthalimido)-r propyl-o-nitrodiphenylamine which is then reduced with hydrogen over palladium-on-carbon in ethanol to give the title compound.
Preparation 3
When in the procedure of Preparation 1, N-3-(l-
phthalimido)propyl-o-aminodiphenylamine is reacted with each of the following acyl chlorides in excess in the manner of /
Preparation A:
2-chloro-berizoyl chloride,
3-chloro-benzoyl chloride,
2-fluoro-benzoyl chloride,
3-fluoro-benzoyl chloride,
2-bromo-benzoyl chloride,
3-bromo-benzoyl chloride, and
4-chloro-benzoyl chloride,
there are obtained:
N-3-(1-phthalimido)propyl-o-(2-chlorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-chlorobenzamido diphenylamine,
N-3-(l-phthalimido)propyl-o-(2-fluorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-fluorobenzamido)
diphenylamine,
206991
N-3-(1-phthalimido)propyl-o-(2-bromobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-bromobenzamido) diphenylamine, and
N-3-(1-phthalimido)propyl-o-(4-chlorobenzamido) d iphenylami ne.
2069
Claims (2)
1. A compound selected from those having the formula: wherein X is selected from the group consisting of hydrogen, chlorine, bromine or fluorine.
2. A compound as claimed in claim 1 as specifically set forth herein. A.H. ROBINS COMPANY By their Attorneys BALDWIN, SON & CAREY fy-H. 0 tint-
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30507681A | 1981-09-24 | 1981-09-24 | |
| NZ198986A NZ198986A (en) | 1981-09-24 | 1981-11-17 | Anti-depressant compositions containing certain 5-(3-amino-propyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ206991A true NZ206991A (en) | 1986-02-21 |
Family
ID=26650497
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ20699281A NZ206992A (en) | 1981-09-24 | 1981-11-17 | 5-(3-aminopropyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines |
| NZ20699181A NZ206991A (en) | 1981-09-24 | 1981-11-17 | N-(3-(phthal-1-imido)propyl)-o-benzamidodiphenylhlamines |
| NZ20699081A NZ206990A (en) | 1981-09-24 | 1981-11-17 | 5-(3-dimethylaminopropyl)-11-phenyl-5h-dibenzo-(b,e)(1,4)-diazepine,fumarate(1:1) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ20699281A NZ206992A (en) | 1981-09-24 | 1981-11-17 | 5-(3-aminopropyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ20699081A NZ206990A (en) | 1981-09-24 | 1981-11-17 | 5-(3-dimethylaminopropyl)-11-phenyl-5h-dibenzo-(b,e)(1,4)-diazepine,fumarate(1:1) |
Country Status (1)
| Country | Link |
|---|---|
| NZ (3) | NZ206992A (en) |
-
1981
- 1981-11-17 NZ NZ20699281A patent/NZ206992A/en unknown
- 1981-11-17 NZ NZ20699181A patent/NZ206991A/en unknown
- 1981-11-17 NZ NZ20699081A patent/NZ206990A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ206990A (en) | 1986-02-21 |
| NZ206992A (en) | 1986-02-21 |
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