US2569814A - beta-haloethylamines - Google Patents

beta-haloethylamines Download PDF

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US2569814A
US2569814A US65508A US6550848A US2569814A US 2569814 A US2569814 A US 2569814A US 65508 A US65508 A US 65508A US 6550848 A US6550848 A US 6550848A US 2569814 A US2569814 A US 2569814A
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James F Kerwin
Glenn E Ullyot
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Smith Kline and French Laboratories Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

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  • This invention relates to new compositions of matter having desirable physiological properties, more particularly adrenolytic or sympatholytic properties.
  • the new compounds according to this invention are p-haloethylamines with the nitrogen linked to the 7-position of the acenaphthene ring system and have the general formula:
  • Z is a member or the group consisting of 1.
  • Alkyl groups having not in excess of 8 carbon atoms i. e., iijethyl, ethyl, propyl, butyl, amyl, hexyl, heptyl a d octyl groups.
  • Aralkyl groups the alkyl' portion of which comprises methylene, ethylene, propylene and butylene radicals, i. er the alkyl portion does not exceed 4 carbon atoms.
  • Substituted aralkyl grou s the alkyl portion of which comprises methylene, ethylene,
  • propylene and butylene radicals i. e... the alkyl portion does not exceed 4 carbon atoms, and the substitution is of a member of the group consisting of:
  • Alkylamino groups the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms.
  • Alkoxyethyl groups the alkoxy portion of which comprises methoxy, ethoxy, propoxy, butoxy, amyloxy, hexyloxy, heptyloxy, and octyloxy groups; i. e., does not exceed 8 carbon atoms.
  • Aryloxyalkyl groups the alkyl portion of which comprises ethylene, propylene, butylene radicals, i. e., does not exceed 4 carbon atoms.
  • aryloxyalkyl groups the alkyl portion of which comprises ethylene, propylene, butylene radicals, i. e., does not exceed 4 carbon atoms and in which the substitution is a member of the group consisting of:
  • Alkoxy groups the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms.
  • Cyclopentylalkyl and cyclohexylalkyl groups the alkyl portion of which comprises methylene, ethylene, propylene, butylene, amylene, Ihexylene.
  • acyl group oi which comprises tormyl, acetyl, propionyl, butyryl, valeryl, caproyl, heptoyl and caprylyl, i. e., does not exceed 8 carbon atoms.
  • Alkylamino groups the alkyl portion 0! which comprises ethyl, methyl, propyl and butyl, i. e.. does not exceed 4 carbon atoms.
  • R, Bi and R are members of the group consisting of hydrogen and alkyl groups consisting oi methyl, ethyl, propyl, butyl, amyl and hexyl. the substituents for R, R1, and Rs being selected so that the sum of the carbon atoms thereoi does not exceed six carbon atoms.
  • 1 is a member or the group consisting of chlorine and bromine.
  • inorganic and organic salts such as will be readily formed with, for example, inorganic and organic acids, such as hydrochloric, sulfuric, sulfamic, tartaric. glycolic, phosphoric, succinic, maleic, hydrobromic, acetic, and the like, are contemplated as included within this invention.
  • inorganic and organic acids such as hydrochloric, sulfuric, sulfamic, tartaric. glycolic, phosphoric, succinic, maleic, hydrobromic, acetic, and the like, are contemplated as included within this invention.
  • the compounds contemplated by this invention may be prepared by various procedure. However, as generally illustrative of procedure for the preparation or the several compounds and as exemplifying preferred procedure for their preparation. they will variously be prepared by a two step process which will be made apparent by the following scheme:
  • the starting material 7-chloroacenaphthene or 7-bromoacenaphthene may be readily prepared by reacting 7- acenaphthenol and thionyl chloride or thionyl bromide in the presence of pyridine.
  • 'I-chloroacenaphthene will melt at 38-39 C.
  • the reaction between 'l-chloroacenaphthene or 'l-bromoacenaphthene and the amino alcohol. i. e., the first step in the process exemplified above, will be carried out conveniently in an inert solvent. such, for example, as benzene, toluene, xylene, or the like.
  • An excess of the amino alcohol may be used to remove the hydrogen halide formed in the reaction or. as will be obvious to those skilled in the art, another acid binding agent may be employed.
  • the amino alcohol product of the first step may be isolated as free base by distilling oi: the solvent or may be converted into a hydrohalide salt by obvious procedure and purified by recrystallization.
  • the intermediate amino alcohol, product or the first step of the process as illustrated is heated with any one of the commonly used agents for replacing a hydroxyl group by a halogen such, for example, as thionyl chloride, thionyl bromide, concentrated hydrobromic acid. concentrated hydrochloric acid, or the like, it being, we believe, apparent that the end product is obtained from the intermediate amino alcohol by replacing the reactive hydroxyl group with chlorine or bromine.
  • a halogen such, for example, as thionyl chloride, thionyl bromide, concentrated hydrobromic acid. concentrated hydrochloric acid, or the like, it being, we believe, apparent that the end product is obtained from the intermediate amino alcohol by replacing the reactive hydroxyl group with chlorine or bromine.
  • the p-chlorethylamine or p-bromethylamine end product is obtained as a hydrohalide salt.
  • the salt may be readily converted to the free base by interaction with one equivalent of a strong base, as, for example, sodium hydroxide, in usual and well known manner, for example, by the addition of the strong base to a cold aqueous solution of the salt.
  • a strong base as, for example, sodium hydroxide
  • the free base may be isolated by rapid extraction into an organic solvent such as ether or benzene.
  • the free base will be reacted in usual well known manner with the appropriate inorganic or organic acid.
  • N-(7-acenaphthenyli-N- ethylaminoethanol hydrochloride Seventeen grams of N-(7-acenaphthenyli-N- ethylaminoethanol hydrochloride is suspended in dry chloroform and a solution of 8.8 g. of thionyl chloride in ml. of chloroformis added with cooling. The reaction mixture is then heated at 35 C. for one-half hour and finally heated to reflux for one and one-half hours. The solvent is removed under reduced pressure and the product N- ('Z-acenaphthenyl) -N-ethyl-fl-chlorethylamine hydrochloride is recrystallized from alcohol and ether. It meltsat 197.5-198 C.
  • the product obtained in the form of its hydrochloride will be readilyconverted tothe free base by treatment thereof in cold aqueous solution with one equivalent of sodium hydroxide in well known manner.
  • the free base may be isolated from the mixture by quickly extracting it with an organic solvent such as ether or benzene.
  • Organic and inorganic .salts will be prepared by adding the desired organic or inorganic acid to a solution of the free base in,-for example, ether, in the usual and well known manner.
  • N- 7-ecendphthenul) -N-benzyl-p-chlorethylamine hydrochloride residue is recrystallized from n-amyl alcohol.
  • N- r 'I-acenaphthenyl) -N-benzylfi-chloroethylamine hydrochloride melts at 196-1975 C.
  • Example 1 N- i-acena hthenul) -N@ (isodaoamyl) p-chtorethylamine hydrochloride
  • the procedure of Example 1 will be used with the ethylaminoethanol replaced by an equimolar amount of isoamylaminoethanol.
  • This compound will be prepared as described under Example 2 except that p-methoxyphenylisopropylaminoethanol will be used instead of benzylaminoethanol.
  • p-Haloethylamines having the structure cnr cn-N-cn-cn-x Number in which Z is a member of the group consisting of lower alkyl groups, lower alkenyl grou s. phenylalkyl groups. the alkyl portion of which does not exceed 4 carbon atoms. methoxy-substi- 'tuted phenylalkyl groups, the alkyl portion of which does not exceed 4 carbon atoms; R1 and R: are members of the group consisting of hydrogen and methyl; and X is a member of the group con-' sisting of chlorine and bromine; and acid addition salts of said compounds.

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

Description

Patented Oct. 2, 1951 2.569.814 fi-HALOETHYLANIINES James F. Kerwin and Glenn E. Ullyot, Philadelphia, Pa., assignors to Smith, Kline & French Laboratories, Philadelphia, Pa, a'corporation of Pennsylvania No Drawing. Application December 15, 1948, Serial No. 65,508
6 Claims. 1
This invention relates to new compositions of matter having desirable physiological properties, more particularly adrenolytic or sympatholytic properties.
The new compounds according to this invention are p-haloethylamines with the nitrogen linked to the 7-position of the acenaphthene ring system and have the general formula:
general formula above such as will be readily formed with, for example, organic and inorganic acids such, as hydrochloric. sulfuric, sultamic, tartaric, hydrobromic, glycolic, phosphoric, succinic, maleic, acetic, and the like.
More specifically within the general formula above, this invention contemplates compounds having the following more specific formula:
in which Z is a member or the group consisting of 1. Alkyl groups having not in excess of 8 carbon atoms, i. e., iijethyl, ethyl, propyl, butyl, amyl, hexyl, heptyl a d octyl groups.
2. Alkenyl groups ving not in excess of 8 carbon atoms, i. e., pr penyl, butenyl, pentenyl, hexenyl, heptenyl and nyl groups.
3. Aralkyl groups the alkyl' portion of which comprises methylene, ethylene, propylene and butylene radicals, i. er the alkyl portion does not exceed 4 carbon atoms.
4. Substituted aralkyl grou s the alkyl portion of which comprises methylene, ethylene,
propylene and butylene radicals, i. e... the alkyl portion does not exceed 4 carbon atoms, and the substitution is of a member of the group consisting of:
(b) Ethyl, methyl, propyl and butyl.
(c) Alkoxy groups, the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms. I
(d) Fluorine.
(e) Bromine.
(f) Chlorine.
(g) Amino groups.
(h) Acylamino groups, the acyl group of which comprises formyl, acetyl, propionyl. butyryl, valeryl, caproyl, heptoyl and caprylyl, i. e., does not exceed 8 carbon atoms.
(1') Alkylamino groups, the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms.
5. Alkoxyethyl groups, the alkoxy portion of which comprises methoxy, ethoxy, propoxy, butoxy, amyloxy, hexyloxy, heptyloxy, and octyloxy groups; i. e., does not exceed 8 carbon atoms.
6. Aryloxyalkyl groups, the alkyl portion of which comprises ethylene, propylene, butylene radicals, i. e., does not exceed 4 carbon atoms.
7. Substituted aryloxyalkyl groups, the alkyl portion of which comprises ethylene, propylene, butylene radicals, i. e., does not exceed 4 carbon atoms and in which the substitution is a member of the group consisting of:
(a) OH.
(b) Ethyl, methyl, propyl and butyl.
(c) Alkoxy groups, the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms.
(d) Fluorine.
(e) Bromine.
(f) Chlorine.
(9) Amino groups.
(h) Acylamino groups, the aoyl group of which comprises formyl, acetyl, propionyl, butyryl, valeryl, caproyl, heptoyl, caprylyl, i. e., does not exceed 8 carbon atoms.
(2') Alkylamino groups, the alkyl portion of which comprises ethyl, methyl, propyl and butyl, i. e., does not exceed 4 carbon atoms.
8. Cyclopentyl and cyclohexyl groups.
9. Cyclopentylalkyl and cyclohexylalkyl groups, the alkyl portion of which comprises methylene, ethylene, propylene, butylene, amylene, Ihexylene.
10. A phenyl group.
55 11. A substituted phenyl group, in which the 3 substitution is a member of thegroup consisting or:
(s) OH. V
(b) Ethyl, methyl. propyl and butyl.
(c) -Allroxy groups, the allql portion or which comprises ethyl, methyl, propyl and butyl, i. e.. does not exceed 4 carbon atoms.
(d) Fluorine.
(e) Bromine.
(I) Chlorine.
(9) Amino groups.
(h) Acylamino groups. the acyl group oi which comprises tormyl, acetyl, propionyl, butyryl, valeryl, caproyl, heptoyl and caprylyl, i. e., does not exceed 8 carbon atoms.
Alkylamino groups, the alkyl portion 0! which comprises ethyl, methyl, propyl and butyl, i. e.. does not exceed 4 carbon atoms.
R, Bi and R: are members of the group consisting of hydrogen and alkyl groups consisting oi methyl, ethyl, propyl, butyl, amyl and hexyl. the substituents for R, R1, and Rs being selected so that the sum of the carbon atoms thereoi does not exceed six carbon atoms.
1: is a member or the group consisting of chlorine and bromine.
The inorganic and organic salts such as will be readily formed with, for example, inorganic and organic acids, such as hydrochloric, sulfuric, sulfamic, tartaric. glycolic, phosphoric, succinic, maleic, hydrobromic, acetic, and the like, are contemplated as included within this invention.
The compounds contemplated by this invention may be prepared by various procedure. However, as generally illustrative of procedure for the preparation or the several compounds and as exemplifying preferred procedure for their preparation. they will variously be prepared by a two step process which will be made apparent by the following scheme:
cm-cn-x E R1 z-N-con It will be appreciated that in the above scheme illustrative of the process for preparing compounds in accordance with this invention X, Z, R1 and R2 represent the atoms in groups as designated with reference to the above general formula for the compounds contemplated by this invention.
In proceeding for the preparation of compounds according to this invention, the starting material 7-chloroacenaphthene or 7-bromoacenaphthene may be readily prepared by reacting 7- acenaphthenol and thionyl chloride or thionyl bromide in the presence of pyridine. By way of example 'I-chloroacenaphthene will melt at 38-39 C.
The reaction between 'l-chloroacenaphthene or 'l-bromoacenaphthene and the amino alcohol. i. e., the first step in the process exemplified above, will be carried out conveniently in an inert solvent. such, for example, as benzene, toluene, xylene, or the like. An excess of the amino alcohol may be used to remove the hydrogen halide formed in the reaction or. as will be obvious to those skilled in the art, another acid binding agent may be employed. The amino alcohol product of the first step may be isolated as free base by distilling oi: the solvent or may be converted into a hydrohalide salt by obvious procedure and purified by recrystallization.
To obtain the end product, the intermediate amino alcohol, product or the first step of the process as illustrated, either as the free base or as a hydrohalide salt, is heated with any one of the commonly used agents for replacing a hydroxyl group by a halogen such, for example, as thionyl chloride, thionyl bromide, concentrated hydrobromic acid. concentrated hydrochloric acid, or the like, it being, we believe, apparent that the end product is obtained from the intermediate amino alcohol by replacing the reactive hydroxyl group with chlorine or bromine.
The p-chlorethylamine or p-bromethylamine end product is obtained as a hydrohalide salt. The salt may be readily converted to the free base by interaction with one equivalent of a strong base, as, for example, sodium hydroxide, in usual and well known manner, for example, by the addition of the strong base to a cold aqueous solution of the salt. The free base may be isolated by rapid extraction into an organic solvent such as ether or benzene.
For the preparation or any desired inorganic or organic salt, the free base will be reacted in usual well known manner with the appropriate inorganic or organic acid.
As more specifically illustrative of compounds in accordance with this invention and of specific procedure for the preparation thereof, the following examples will exempliiy compounds of the several types contemplated and procedure for the preparation thereor and will, in connection with the foregoing general definition of the compounds contemplated and their preparation, make apparent to those skilled in the art the structure oi. all the several compounds contemplated by this invention and procedure for their preparation:
EXALCPLEI N-(7-acenaphthenul) -N-ethyl-p-chlorethulamine hydrochloride cm-cn-N-cm-cmcmc:
Seventeen grams of N-(7-acenaphthenyli-N- ethylaminoethanol hydrochloride is suspended in dry chloroform and a solution of 8.8 g. of thionyl chloride in ml. of chloroformis added with cooling. The reaction mixture is then heated at 35 C. for one-half hour and finally heated to reflux for one and one-half hours. The solvent is removed under reduced pressure and the product N- ('Z-acenaphthenyl) -N-ethyl-fl-chlorethylamine hydrochloride is recrystallized from alcohol and ether. It meltsat 197.5-198 C.
The product obtained in the form of its hydrochloride will be readilyconverted tothe free base by treatment thereof in cold aqueous solution with one equivalent of sodium hydroxide in well known manner. The free base may be isolated from the mixture by quickly extracting it with an organic solvent such as ether or benzene.
Organic and inorganic .salts will be prepared by adding the desired organic or inorganic acid to a solution of the free base in,-for example, ether, in the usual and well known manner.
EXAMPLE-2 N- 7-ecendphthenul) -N-benzyl-p-chlorethylamine hydrochloride residue is recrystallized from n-amyl alcohol. N- r 'I-acenaphthenyl) -N-benzylfi-chloroethylamine hydrochloride melts at 196-1975 C. v
The free base and inorganic and organic salts thereof will be obtained as heretofore made perfectly apparent.
EXAMPLE 3 N- (7-dce1 i aphthenyl) Jimihgvt-p-bhlorethylamine hydrochloride This compound will be prepared by the procedure of Example 1 using an equivalent amount of methylaminoethanol instead of ethylaminoethanol.
The free base and inorganic and organic salts thereof will be obtained as heretofore made perfectly apparent.
N- i-acena hthenul) -N@ (isodaoamyl) p-chtorethylamine hydrochloride The procedure of Example 1 will be used with the ethylaminoethanol replaced by an equimolar amount of isoamylaminoethanol.
The free base and inorganic and organic salts thereof will be obtained as heretofore made perfectly apparent.
N- (7-aeenaphthen1 l) -N dllyl -p-ohlorethulamine hydrochloride CHx-CH-N-CHr-CHz-CLHC] This compound will be made in the same manher as Example 1 except that 1-ethylamino 2- propanol will replace ethylaminoethanol in the first step of the synthesis. q The free base and inorganic and organic-salts thereof will be obtained as heretofore made perfectly apparent.
' EXAMPLE? N.- (7-acenap thenvl) methane-amm- 1-chloropr mne hydrochloride The procedure'of Example 1 will be followed with2-ethylamino-1-propanol used in place of ethylaminoethanol. I
The free base and inorganic and organic salt: thereof will be obtained as heretofore made perfectly apparent.
EXAMPLE8 OCH:
This compound will be prepared as described under Example 2 except that p-methoxyphenylisopropylaminoethanol will be used instead of benzylaminoethanol.
The free base and inorganic and organic salts thereof will be obtained as heretofore made perfectly apparent.
From the above general and specific disclosure all of the several'compounds and inorganic and organic salts thereof contemplated by this invention are made perfectly apparent to those skilled in-the art, it being only necessary for the chemist to substitute the atoms and groups, all of which are common and well known to the chemist, corresponding to any particular compound or salt thereof in the general formulae given.
From the foregoing general and specific disclosure of procedure for the preparation of the compounds and salts thereof contemplated by this invention, it is apparent to those skilled in the art that all the compounds and salts will be prepared by the procedure described and exemplified by the mere use in step 1 of the reagents corresponding to any particular compound desired, the reagents for any particular compound being either well known or prepared by the procedure indicated and affording no problem to the chemist.
As ha been indicated, while in the foregoing examples the products in accordance with this invention are exemplified by their hydrochloride salts, the several examples will serve as specific examples of free bases by the mere elimination from the several formulae given of the radical 1101. As has been indicated, the free bases will be obtained from the hydrohalide salts by usual and well known procedure comprising treatment with an inorganic base such as sodium carbonate, sodium hydroxide, or the like. The above general formula will serve as specifically exemplifying all the several compounds embraced thereby by a mere substitution in the formula for Z, R1, R: and X of the substituents given therefor in connection with the formula.
What we claim and desire to protect by Letters Patent is:
1. p-Haloethylamines having the structure cnr cn-N-cn-cn-x Number in which Z is a member of the group consisting of lower alkyl groups, lower alkenyl grou s. phenylalkyl groups. the alkyl portion of which does not exceed 4 carbon atoms. methoxy-substi- 'tuted phenylalkyl groups, the alkyl portion of which does not exceed 4 carbon atoms; R1 and R: are members of the group consisting of hydrogen and methyl; and X is a member of the group con-' sisting of chlorine and bromine; and acid addition salts of said compounds. I
2. A compound having the formula:
3. A compound having the formula:
CHrCH-N-CHr-C :CLHCI 4. A compound having the formula:
CHg-CH-N-CHr-ClIs-CLHCI 5. A compound having the formula:
CHz-CH-N-CHa-CHr-CLHC] Ha ts 6. A compound having the formula:
cm ca-m-cm-cH-cmncl JALIES F. KERWIN: GLENN E. ULLYOT.
REFERENCES CITED The following references are of record in the file of this patent:
FOREIGN PATENTS Country Date Austria Apr. 15, 1933 OTHER REFERENCES Achenbach et al.. Fed. Proc., vol. 6, pp. 304-305. Hunt: J. Pharm. Exp. Therapy, vol. 95, pp. 177- 184.

Claims (1)

1. B-HALOETHYLAMINES HAVING THE STRUCTURE
US65508A 1948-12-15 1948-12-15 beta-haloethylamines Expired - Lifetime US2569814A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2070103A1 (en) * 1969-10-01 1971-09-10 Squibb & Sons Inc Antiphlogistic 1- (hydroxy amido or amino) - acenaphthenes
US4806671A (en) * 1986-05-07 1989-02-21 E. I. Du Pont De Nemours And Company Substituted acenaphthenes and their use as inhibitors of phospholipase A2

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2070103A1 (en) * 1969-10-01 1971-09-10 Squibb & Sons Inc Antiphlogistic 1- (hydroxy amido or amino) - acenaphthenes
US4806671A (en) * 1986-05-07 1989-02-21 E. I. Du Pont De Nemours And Company Substituted acenaphthenes and their use as inhibitors of phospholipase A2

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