US2740779A - Substituted azacycloalkanes - Google Patents
Substituted azacycloalkanes Download PDFInfo
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- US2740779A US2740779A US2740779DA US2740779A US 2740779 A US2740779 A US 2740779A US 2740779D A US2740779D A US 2740779DA US 2740779 A US2740779 A US 2740779A
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- United States
- Prior art keywords
- ether
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- mole
- acid
- alkyl
- Prior art date
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- 150000003976 azacycloalkanes Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 24
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N Azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 150000003839 salts Chemical class 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- -1 4-cyano compound Chemical class 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000007792 addition Methods 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000001225 therapeutic Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- MFESCIUQSIBMSM-UHFFFAOYSA-N 1-bromo-3-chloropropane Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N Bromate Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 229940049954 Penicillin Drugs 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003868 ammonium compounds Chemical group 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000000202 analgesic Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000626 benzylpenicillin Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- nesium halide is prepared from 0.070 g-atom of magnesium 2 740 779 metal and 0.075 mole of alkyl halide in 100 ml. of dry ether. To this solution is added dropwise 0.05 mole of SUBSTITUTED AZACYCLOALKANES the appropriate 4-cyano compound in 100 ml. of toluene.
- the compounds falling with the scope of the invention 297,185 by reacting the appropriate base with the desired are specific members of the more general group of cominorganic or organic carboxylic acid. Preferred acids are pounds and claimed in application Serial No. 297,185, filed those mentioned in said prior application These cyclic July 3, 1952.
- the present compounds may be represented bases fi also callable of reacting alkyl halides On by the general f l an equlmolar basis under normal conditions to form quaternary ammonium compounds.
- the mixture was then allowed to warm to room temperature and stand overnight
- the precipitated inorganic salts were filtered off and the ether distilled from the filtrate at reduced pressure.
- the yellow liquid residue contained the 1,6-amino-chloride (I) with R1 representing a lower alkyl and R2 standing for either hydrogen or an alkyl while A is an anion, R standing for an aryl group and with R3 and R4 each standing for hydrogen or lower alkyl and R5 representing a lower alkyl group.
- R which represents an aryl radical
- the latter may be either a subtituted or unsubstituted phenyl ring.
- Preferred substituents on a ring which may be in any position and ranging from 1 to 3 are lower alkyl, lower alkoxy, halogen, nitro, hydroxy, aliphatic acyl and acyloxy,
- an especially preferred radical because it imparts valuable therapeutic action to 6 i was diisolved m 180 of benzonitrfle and the i the compound is the m hydroxy phenyl radicaL In 5 sulting solution heated at C. for 20 hours.
- the mixeral, the compounds of the invention may b d in the ture was cooled, ml. of acetone added, and the premanner disclosed in the earlier filed application Serial cipitated quaternary salt (H) was filtered 05 after Stand- No. 297,185.
- a general procedure for making specific ing 4 hOuIS- 4-acyl compounds utilizes the cyano compound obtained 70 for C16H23C1N20; from Reaction 3 disclosed in said earlier case. In such N, 9.51; C1, 12 Found; N, general procedure, an ether solution of the alkyl mag- Cl, 12.18.
Description
7 amino and mono and di-lower alkyl-substituted amino rad- 2,740,779 Patented Apr. 3, 1956 nesium halide is prepared from 0.070 g-atom of magnesium 2 740 779 metal and 0.075 mole of alkyl halide in 100 ml. of dry ether. To this solution is added dropwise 0.05 mole of SUBSTITUTED AZACYCLOALKANES the appropriate 4-cyano compound in 100 ml. of toluene.
5 D Julius Diamond Philadelphia and William F. Bruce, The temperature 1sma1nta1ned,w1thst1rr1ng, at 25 35 C during the addition. On its completion, the temperature is gggg gzgafgfasfi ggflf ?t g gg gfififi Egg gradually raised by distilling off the ether. A maximum ware temperature of 65-85 C. is maintained for 6 hours. The mixture is cooled and extracted with dilute hydrochloric N0 gl p January 5, 1954, 10 acid. The acid extract is washed with ether, then basisenal 402,397 fied with ammonium hydroxide, and finally extracted with 2 Claims (C1. z chloroform. The chloroform extract is dried over anhydrous sodium sulfate, filtered, and concentrated. Vacuum distillation of the residue gives the desired aminoketone This invention relates to the preparation of cyclic comhas?" PoundS and more Particularly the Preparation of y Acid addition salts of the cyclic bases may be made in Ycloalkanes. well known manner as disclosed in Application Serial No.
The compounds falling with the scope of the invention 297,185 by reacting the appropriate base with the desired are specific members of the more general group of cominorganic or organic carboxylic acid. Preferred acids are pounds and claimed in application Serial No. 297,185, filed those mentioned in said prior application These cyclic July 3, 1952. The present compounds may be represented bases fi also callable of reacting alkyl halides On by the general f l an equlmolar basis under normal conditions to form quaternary ammonium compounds.
O The reaction is carried out in the prsence of inert solvent.
H I For a more specific description of the process, the following reactions illustrate the formation of the specific compound 4-propionyl-4-m-hydroxyphenyl-l-methylaza- CHPC cylcoheptane. (IN ON rn-CH3OCH -CHCH;CH5N(CH:)2 NaNH m-CH3OCsH4( JCH CHzN(CH;)z CQHgCN ether 100 BYCHCHQCHQC! HgCHnCHr-Cl CN OH HI CHHO CUHA (IJCHQCHQ CH3 m-CHCQH4J)-CH2CH 200250 EtMgBr N 01- GE; 3 mm ether HgCHgC 9 CH; CHCHIO a (III) COCHQCH; COCHzCHa m-CHaO-CsHr CHICHQ HB m-HOCuHr- -CH&CH2
I NCH: NCHa CHQCHQCQQ H2CH2CH2 wherein X stands for either N-R1 or 4-cyano-4-m-methoxyphenyl-N-methylazacycloheptane /R methochloride (Compound ll).
N-A A solution of 0.181 mole (39.5 g.) of Z-(m-methoxyphenyl)-4-dimethylamino-butyronitrile in 250 ml. of ether was added to a stirred suspension of 0.217 mole (8.5 g.) of sodamide in 250 ml. of other at such a rate as to maintain gentle refluxing. The operations were carried out in a nitrogen atmosphere. Refluxing and stirring were contined for 2 additional hours. The mixture was cooled to 30 C., and 0.199 mole (31.5 g.) of trimethylene chlorobromide in 100 ml. of ether was added dropwise at 25 C. to --15 C. while stirring. The mixture was then allowed to warm to room temperature and stand overnight The precipitated inorganic salts were filtered off and the ether distilled from the filtrate at reduced pressure. The yellow liquid residue contained the 1,6-amino-chloride (I) with R1 representing a lower alkyl and R2 standing for either hydrogen or an alkyl while A is an anion, R standing for an aryl group and with R3 and R4 each standing for hydrogen or lower alkyl and R5 representing a lower alkyl group.
With regard to R which represents an aryl radical, the latter may be either a subtituted or unsubstituted phenyl ring. Preferred substituents on a ring which may be in any position and ranging from 1 to 3 are lower alkyl, lower alkoxy, halogen, nitro, hydroxy, aliphatic acyl and acyloxy,
icals. As will be indicated later, an especially preferred radical because it imparts valuable therapeutic action to 6 i was diisolved m 180 of benzonitrfle and the i the compound is the m hydroxy phenyl radicaL In 5 sulting solution heated at C. for 20 hours. The mixeral, the compounds of the invention may b d in the ture was cooled, ml. of acetone added, and the premanner disclosed in the earlier filed application Serial cipitated quaternary salt (H) was filtered 05 after Stand- No. 297,185. A general procedure for making specific ing 4 hOuIS- 4-acyl compounds utilizes the cyano compound obtained 70 for C16H23C1N20; from Reaction 3 disclosed in said earlier case. In such N, 9.51; C1, 12 Found; N, general procedure, an ether solution of the alkyl mag- Cl, 12.18.
4 cyan-4 m-meth0xyphenyl-N-methylazacycloheptane (Compound III) Into a small Claisen flask setup for distillation, was placed 0,085 mole (25 g.) of the quaternary salt (II).
4 with chloroform. The extract was dried, filtered, and distilled. At 190-2Q0 C. (0.3 mm.) 3.3 g. of a yellow viscous syrup distilled over. On cooling the material became glassy. It was dissolved in boiling ether, filtered,
Aft'erevacuatingthe systemyto 1--3 mm., heat'wa'sta'pplied 5 and t filtrate concentrated a small volume on useing an air-bath. At a bath temperature (if-"200450" standlpg tempera-me the P? duct. (V) appeared c. a liquid distilled over at 170-210 c. Redis'tillation. as Whlte .qystals- Thermlxmre l crystal? gave the 'cyano base (III), B. P.3l5'0- -154" C. (0.3 mm.'), Washed with r ii i ai li 1 1 nbzg 153.352 2.422 1.062. tpurple color with aqueousmlcohohcternc chloride S0l110l'1. jgf gff fgg gfiflfig; gjg gi fi' f gg Anal.-Calcd. for C16H2NO22 c, 73150; H, 8.86; 'N, 5.36. Found: C, 73.92; H, 9.05; N, 5.53.
D I Other compounds falling within the scope of the inven- -1 i y -m yp n m wy tion are given in the'following table with identifying charheptlme p acteristics. The various radials .R,-R3, R4 and R5 are vEthyl magmas-Him bromide was .pwpare-d from specific species of the general "formula given hereinbelow. g-ato'm (-2.2 g.) of magnesium metal and 0.10 mole RFCO R (10.9 g.) of ethyl bromide in 150 ml. ether. To this solu- I I don was added, with stirring, 0.0573 mole -14 g.) or the f' E cyano'b'ase (III) in 150 ml. of ether at such a rate as 20 to maintain gentle refluxing. After 5 additional hours R Ra R4 R5 3 nn( 0.) Derivative, M. P.
- 0.11. a H 2 i 1180MB) ifil fii fidiflii 'cim H H, 11-03111 132-3 1. 5300 (26) i plcrate,13840. 0 11i H OH; 2H 135-42 1.'5350(-27.'5) methlodide, 183-5". .C Hs CH3 H C H 13342 1. 5400 (27) 3 pierate,1645 d.
of stirring and refluxing, the mixture was allowed to stand The cyclic free bases 'are useful for the formation of overnight. The cooled mixture was extracted with aquequaternary ammonium compounds since they readily reous hydrochloric acid, the acid extract basified with amact with an alkyl halide, particularly the long chain alkyl monium hydroxide, extracted with ether, and the "ether halides, to form valuable wetting'a'gents. These bases 'or extract dried, filtered, and concentrated under reduced their acid-addition'salts are also capable of reacting with pressure. A light yellow liquid residue remained which penicillin to form substantially water-insoluble salts contained the crude ketobase (IV). thereof. In addition, many of the bases or their salts demonstrate varying degrees of analgesic action and thus 4-propzanyl-4-m-hydroxyphenyl-methylazacycloheptane are useful .therapeutics (Compound V) 40 We claim:
The above compound (IV) was usedwithout further The compound 12'd1methy1'4'phenyl'4'proplonyl purification. It was dissolved in T00 ml. of 48% hydroazacycloheptane' bromic acid. The solution was heated to reflux and kept A compoufld of the group conslstmg of 12'd1methy1' at this temperature (110425.. a) for 17 The 4-phenyl-4-prop1onyl azacycloheptane and salts thereof.
cooled solution was treated with 230 ml. of 4.N-'sodi-um hydroxide solution and the resultingfsolution washed with ether. The aqueous alkaline solution was saturated with carbon dioxide to precipitate an oil which was extracted References Cited in the file of this patent UNITED STATES PATENTS 2,666,050 Diamond et al. Jan. 12, 1954
Claims (1)
- 2. A COMPOUND OF THE GROUP CONSISTING OF 1,2-DIMETHYL4-PHENYL-4-PROPIONYL AZACYCLOHEPTANE AND SALTS THEREOF.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2740779A true US2740779A (en) | 1956-04-03 |
Family
ID=3445653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2740779D Expired - Lifetime US2740779A (en) | Substituted azacycloalkanes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2740779A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347866A (en) * | 1965-06-22 | 1967-10-17 | Upjohn Co | 4-(indol-3-yl)-hexahydro-1h-azepines and their method of preparation |
| FR2015812A1 (en) * | 1968-08-16 | 1970-04-30 | Wyeth John & Brother Ltd | Analgesic hexahydro 1h azepine derivs |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666050A (en) * | 1954-01-12 | Process of producing them |
-
0
- US US2740779D patent/US2740779A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666050A (en) * | 1954-01-12 | Process of producing them |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347866A (en) * | 1965-06-22 | 1967-10-17 | Upjohn Co | 4-(indol-3-yl)-hexahydro-1h-azepines and their method of preparation |
| FR2015812A1 (en) * | 1968-08-16 | 1970-04-30 | Wyeth John & Brother Ltd | Analgesic hexahydro 1h azepine derivs |
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