CA1177491A - Process for the preparation of 2-¬¬¬5- (dimethylamino)methyl-2-furanylmethylthio furanyl|methyl|thio|ethaneamine ethaneamine - Google Patents
Process for the preparation of 2-¬¬¬5- (dimethylamino)methyl-2-furanylmethylthio furanyl|methyl|thio|ethaneamine ethaneamineInfo
- Publication number
- CA1177491A CA1177491A CA000429776A CA429776A CA1177491A CA 1177491 A CA1177491 A CA 1177491A CA 000429776 A CA000429776 A CA 000429776A CA 429776 A CA429776 A CA 429776A CA 1177491 A CA1177491 A CA 1177491A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- thio
- dimethylamino
- ethaneamine
- furanyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
ABSTRACT
A new process for the preparation of 2-[[[5-(dimethyl-aminol-methyl-2-furany] methy] thio]ethaneamine of the formula is described, wherein 2-[[[5-(dimethylamino)methyl-2-furany] -methyl] thio]ethanol of the formula is halogenated to the corresponding halogenide of the formula wherein Hal is chlorine or bromine, and the resulting compound is aminated with ammonia to yield the desired compound.
The desired compound represents a valuable intermediate for the preparation of the therapeutically important compound ranitidine, which is used for the treatment of ulcer diseases.
A new process for the preparation of 2-[[[5-(dimethyl-aminol-methyl-2-furany] methy] thio]ethaneamine of the formula is described, wherein 2-[[[5-(dimethylamino)methyl-2-furany] -methyl] thio]ethanol of the formula is halogenated to the corresponding halogenide of the formula wherein Hal is chlorine or bromine, and the resulting compound is aminated with ammonia to yield the desired compound.
The desired compound represents a valuable intermediate for the preparation of the therapeutically important compound ranitidine, which is used for the treatment of ulcer diseases.
Description
774gl A P~OCESS FO~ T~E ~EP~ATION OF 2-[[[5~(DIMETHyLAMINo)METH~L
2-FURA~YL] METHYL~ THIO] ETHANEAMINE
The present invention relates to a new process for the preparation of 2-[[[5~(dimethylamino)methyl-2 furany~ methyl]thio]
ethaneamine of the formula o
The present invention relates to a new process for the preparation of 2-[[[5~(dimethylamino)methyl-2 furany~ methyl]thio]
ethaneamine of the formula o
3~NCH2 i ~2scH2cH2NH2 This compound is a valuable intermediate in the synthesis of N-[2-[[[5-(dimethylamino)methyl~2~furanyl]methyl~thio]ethyl]-N~-meth 2-nitro-1,1-ethenediamine, a compound known under the genaric name ranitidine, Ranit~dine was first described in the German Publication 27 34 070 as a selective H2-antagonist, i.e. a compound which in-hibits the secretion of gastric acid, which is stimulated by the histamine-H2~receptoxs. Ranitidine represents preferably in the form of its hydrochloride, a valuable medicine for the treatment of ulcer diseases, The above-stated German Publication also describes a method for the synthesis of the intermediate 2-[[[5-(dimethylamino)-methyl-2-furany~ methyl] thio~ ethaneamine, wherein the starting compound 5-(N,N-dimethylamino)-methyl-2-hydroxymethylfuran of the formula (CH3)2NCH2 / ~ / CH2 is reacted with cisteamine-hydrochloride (Example A of the mentioned German Publication), the yield being 54%. The starting compound 5-(N,N~dimethylamino)methyl-2-hydroxy-,;, , ; .
.~ . . . ~ .
,, ~ ' .
.
~ 2 ~ ~ 177~9~
methylfuran is a known compound, which can be o'btained ingood yield (70 %) from 2-furan-methanol (furfuryl alcohol) by means of Mannich's reaction in the manner described by Gill and Ing, J.Chem.Soc. 4728-4731 (1958).
A disadvantage oP this method resides in the use of c-ysteamine hydrochloride, which is an extremely expensive chemical.
~urthermore, the yields of the reaction are poor. ~dditionally, the reaction takes up quire a long period of time.
~he object of the present invention is to provide a process for the preparation of 2-[[[5-(dimethylamino)methyl-2-furanyl]-methyl]thio~ethaneamine with good yield, avoiding the use of the extremely expensive and not readily available cysteamine hydrochloride and thereby substantially affec-ting the economy of the reaction.
4ccording to the invention this object is achieved by reacting 2-[[[5-(dimethylamino)me-thyl-2-furanyl~methyl~thio~ethanol of the formula (CH3)21~C~2 ~ CH2SCH2CHzO~I
with SOCl2 in methylene chloride or with a solution of HBr in acetic acid to give the corresponding halogenide of the formula (Ci3)2NGl2 CH2SCll2C~2-~lal wherein ~al is preferably chlorine or bromine, whereupon the thus obtained compound is amina-ted with ammonia to yield 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl~-thio]ethaneamine of - - ~ - ~ . .
, .
- ~- 1177~gl the formula (CH3)2NCH2 ~ ~ CI~2scH2c~I2NH2 The starting co~pound 2-[[[5-(dimethylamino)methyl-2-furanyl~-methyl]thio~ethanol can be obtained in accordance with the known methods from 5-(N,N-dimethylamino)met'nyl-2-hydroxymethyl furane or from 2-[[[2-furanylimethyl]thi.o~ethanol.
The invention is illustrated by the following non-limitative Examples.
, :
: :
;, . , .
: - ; : ~ .
7 ~ ~ g l Example 1 2-[[[5-(dimeth~lamino)meth~Jl-2-furan~l~m_t~I~lJthio~ethanechloride h~drochloride 2-[[~5-(dimethylamino)methyl-2--fur~nyl~methglJthio]ethanol (0.5 g, 2.3 mmole) is dissolved in methylene chloride (7 ml).
A solution of SOC12 (0.5 ml) in methylene chloride (3 ml) -is added dropwise under stirring at room temperature. After 30 minutes the reac-tion mixture is evaporated. There are obtained 0.42 g of the crude product.
~xample 2 2-[[[5-(dimeth~lamino)meth~l-2 fur~yl~meth~l]thio]ethaneamine Crude 2-[[[5-(dimethylamino)methyl-2-furanyl~methyl]thio~ethane-chloride hydrochloride (0.42 g) obtained in Example 1 is dissolved in methanol (30 ml). The solution is refluxed while passing through it gaseous ammonia Eor 4 to 5 hours. The solvent is then evaporated, the oily residue is dissolved in the least possible ~uantity of wa-ter, the resulting solution is n~utralized with Na2C03 and extracted with ether. The etherial extracts are dried with Na2S04, filtered and evaporated. Thus there are obtained 214 mg of the desired compolmd (46 % with respect to 2-[[[5-(dimethylamino)methyl-2-furanyl~methyl]-thio~ethanol). Bop~ 104-106C (0.133 mbar).
.
. . ~ . .
~ . ~
, ;, . , , 1 1~7~91 Example ~
2-[[C~N,N-dimeth~lamino)meth~l-2-furan~l~meth~l~thio]ethane~
chloride 2-[[[5-~N t N dimethylamino)methyl-2-furanyl~methylJthio]ethanol (2.15 g, 10 mmole) is dissolved in methylene chloride (18 ml).
A solution of thionyl chloride (2.18 ml, 30 mmole) in methylene chloride (9 ml) is added -thereto dropwise under stirring at room temperature. ~he solution is stirred for another hour at room temperature. The solvent is evaporated and methanol (25 ml), saturated with ammonia, is poured on the red oily residue. Active charcoal (100 mg) is added thereto and the resulting mixture is filtered after 1 hour. The solvent is evaporated, ethyl acetate is poured on the residual crude product, it is filtered and ethyl acetate is evaporated. There are obtained 1.84 g (79 %) of the desired product.
Rf = 0.58 (CHCl3 : MeOH = 5 : 1) MS: m/e = 233 (M+) H NMR (CDC13):9~ = 7-75 (s, -N(CH3)2); 7.05 - 7035 and 6-45 -6.7 (two t, -CH2-CH2); 5.6 and 6.25 (two s, -CH2-);
3.9 (s, H3 4) JCH2CH2- 7.5 H
Example 4 2-C[[5-(N~N-dimethyl-amino~methyl-2-furanylJmethyl]thio]ethane chloride oxalate Oxalic acid dihydrate (540 mg) is dissolved in ethyl acetate (30 ml). A solution of 2-~[[5-(N,N-dimethylamino)methyl-2-furanyl~methyl]thio]ethanechloride (l g) in ethyl acetate is added dropwise thereto. l'he product which separated is sucked off. There are obtained 0.94 g of the corresponding oxalate, m.p. 87-91C.
H NMR (DMSO -d6):~ = 7.35 (s, -~(CH3)2); 7.2 and 6.3 (-two t, -CH2-CH2-); 6.15 and 5.85 (two s, -CH2); 3.7 and 3.5 (d, H3 L~); 1.0 (broad, OH) .
:: ` , ., :
- ~ - 6 ~ 1l77491 3,4 JCM = 7-5 Hz ~nalysis for C12H18ClNOS
CalC.: 44.51 % C 5.60 ~/o H 4.33 'yo N
Found: 45.41 % C 5.30 ~/o H 4.76 '~o N
~xample 5 2-~[[~-(N,N-dimeth,ylamino~meth;yl-?--furan;yl~meth~l~-thio~ethane amine Aqueous a~onia solution (50 ml) is poured on 2-[[[5-(N,N-dimethylamino)methyl-2-furanyl~methyl]thio]ethanechloride (640 mg, 2.7 mmole? and it is stirred for 12 hours at room temperature. ~he resulting aqueous solu-tion is extracted with ethyl acetate (4 x 30 ml). The combined extracts are dried o-ver Na2S04 and the solvent is evaporated. ~here are obtained 440 g (75 %) of the desired compound. The NMR~ IR and MS of this compound correspond to those of the authentic compound.
Exa~ple 6 ., 2-[[[5-(N,N-dimeth~lamino)meth~l-2 furan;Yl]meth~l]thio~ethane-amine dioxalate Oxalic acid (518 mg) is dissolved in ethyl ace-tate (26 ml).
A solution of 2-[[[5-(N,N-dimethylamino)methyl-2-furanyl]methyl~-thio]ethaneamine (440 mg, 2.1 mmole) in ethyl acetate is added dropwise thereto. ~he product which separates is sucked off.
There are obtained 690 mg (85 %) of the corresponding dioxalate, m.p. 160-163C. ;
Analysis for C14H22N209S:
Calc.: 42.53 % C 5.61 % H 7.08 % N
Found: 42.55 % C 5.76 C/o H 7.24 % N
-'' ' . : '
.~ . . . ~ .
,, ~ ' .
.
~ 2 ~ ~ 177~9~
methylfuran is a known compound, which can be o'btained ingood yield (70 %) from 2-furan-methanol (furfuryl alcohol) by means of Mannich's reaction in the manner described by Gill and Ing, J.Chem.Soc. 4728-4731 (1958).
A disadvantage oP this method resides in the use of c-ysteamine hydrochloride, which is an extremely expensive chemical.
~urthermore, the yields of the reaction are poor. ~dditionally, the reaction takes up quire a long period of time.
~he object of the present invention is to provide a process for the preparation of 2-[[[5-(dimethylamino)methyl-2-furanyl]-methyl]thio~ethaneamine with good yield, avoiding the use of the extremely expensive and not readily available cysteamine hydrochloride and thereby substantially affec-ting the economy of the reaction.
4ccording to the invention this object is achieved by reacting 2-[[[5-(dimethylamino)me-thyl-2-furanyl~methyl~thio~ethanol of the formula (CH3)21~C~2 ~ CH2SCH2CHzO~I
with SOCl2 in methylene chloride or with a solution of HBr in acetic acid to give the corresponding halogenide of the formula (Ci3)2NGl2 CH2SCll2C~2-~lal wherein ~al is preferably chlorine or bromine, whereupon the thus obtained compound is amina-ted with ammonia to yield 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl~-thio]ethaneamine of - - ~ - ~ . .
, .
- ~- 1177~gl the formula (CH3)2NCH2 ~ ~ CI~2scH2c~I2NH2 The starting co~pound 2-[[[5-(dimethylamino)methyl-2-furanyl~-methyl]thio~ethanol can be obtained in accordance with the known methods from 5-(N,N-dimethylamino)met'nyl-2-hydroxymethyl furane or from 2-[[[2-furanylimethyl]thi.o~ethanol.
The invention is illustrated by the following non-limitative Examples.
, :
: :
;, . , .
: - ; : ~ .
7 ~ ~ g l Example 1 2-[[[5-(dimeth~lamino)meth~Jl-2-furan~l~m_t~I~lJthio~ethanechloride h~drochloride 2-[[~5-(dimethylamino)methyl-2--fur~nyl~methglJthio]ethanol (0.5 g, 2.3 mmole) is dissolved in methylene chloride (7 ml).
A solution of SOC12 (0.5 ml) in methylene chloride (3 ml) -is added dropwise under stirring at room temperature. After 30 minutes the reac-tion mixture is evaporated. There are obtained 0.42 g of the crude product.
~xample 2 2-[[[5-(dimeth~lamino)meth~l-2 fur~yl~meth~l]thio]ethaneamine Crude 2-[[[5-(dimethylamino)methyl-2-furanyl~methyl]thio~ethane-chloride hydrochloride (0.42 g) obtained in Example 1 is dissolved in methanol (30 ml). The solution is refluxed while passing through it gaseous ammonia Eor 4 to 5 hours. The solvent is then evaporated, the oily residue is dissolved in the least possible ~uantity of wa-ter, the resulting solution is n~utralized with Na2C03 and extracted with ether. The etherial extracts are dried with Na2S04, filtered and evaporated. Thus there are obtained 214 mg of the desired compolmd (46 % with respect to 2-[[[5-(dimethylamino)methyl-2-furanyl~methyl]-thio~ethanol). Bop~ 104-106C (0.133 mbar).
.
. . ~ . .
~ . ~
, ;, . , , 1 1~7~91 Example ~
2-[[C~N,N-dimeth~lamino)meth~l-2-furan~l~meth~l~thio]ethane~
chloride 2-[[[5-~N t N dimethylamino)methyl-2-furanyl~methylJthio]ethanol (2.15 g, 10 mmole) is dissolved in methylene chloride (18 ml).
A solution of thionyl chloride (2.18 ml, 30 mmole) in methylene chloride (9 ml) is added -thereto dropwise under stirring at room temperature. ~he solution is stirred for another hour at room temperature. The solvent is evaporated and methanol (25 ml), saturated with ammonia, is poured on the red oily residue. Active charcoal (100 mg) is added thereto and the resulting mixture is filtered after 1 hour. The solvent is evaporated, ethyl acetate is poured on the residual crude product, it is filtered and ethyl acetate is evaporated. There are obtained 1.84 g (79 %) of the desired product.
Rf = 0.58 (CHCl3 : MeOH = 5 : 1) MS: m/e = 233 (M+) H NMR (CDC13):9~ = 7-75 (s, -N(CH3)2); 7.05 - 7035 and 6-45 -6.7 (two t, -CH2-CH2); 5.6 and 6.25 (two s, -CH2-);
3.9 (s, H3 4) JCH2CH2- 7.5 H
Example 4 2-C[[5-(N~N-dimethyl-amino~methyl-2-furanylJmethyl]thio]ethane chloride oxalate Oxalic acid dihydrate (540 mg) is dissolved in ethyl acetate (30 ml). A solution of 2-~[[5-(N,N-dimethylamino)methyl-2-furanyl~methyl]thio]ethanechloride (l g) in ethyl acetate is added dropwise thereto. l'he product which separated is sucked off. There are obtained 0.94 g of the corresponding oxalate, m.p. 87-91C.
H NMR (DMSO -d6):~ = 7.35 (s, -~(CH3)2); 7.2 and 6.3 (-two t, -CH2-CH2-); 6.15 and 5.85 (two s, -CH2); 3.7 and 3.5 (d, H3 L~); 1.0 (broad, OH) .
:: ` , ., :
- ~ - 6 ~ 1l77491 3,4 JCM = 7-5 Hz ~nalysis for C12H18ClNOS
CalC.: 44.51 % C 5.60 ~/o H 4.33 'yo N
Found: 45.41 % C 5.30 ~/o H 4.76 '~o N
~xample 5 2-~[[~-(N,N-dimeth,ylamino~meth;yl-?--furan;yl~meth~l~-thio~ethane amine Aqueous a~onia solution (50 ml) is poured on 2-[[[5-(N,N-dimethylamino)methyl-2-furanyl~methyl]thio]ethanechloride (640 mg, 2.7 mmole? and it is stirred for 12 hours at room temperature. ~he resulting aqueous solu-tion is extracted with ethyl acetate (4 x 30 ml). The combined extracts are dried o-ver Na2S04 and the solvent is evaporated. ~here are obtained 440 g (75 %) of the desired compound. The NMR~ IR and MS of this compound correspond to those of the authentic compound.
Exa~ple 6 ., 2-[[[5-(N,N-dimeth~lamino)meth~l-2 furan;Yl]meth~l]thio~ethane-amine dioxalate Oxalic acid (518 mg) is dissolved in ethyl ace-tate (26 ml).
A solution of 2-[[[5-(N,N-dimethylamino)methyl-2-furanyl]methyl~-thio]ethaneamine (440 mg, 2.1 mmole) in ethyl acetate is added dropwise thereto. ~he product which separates is sucked off.
There are obtained 690 mg (85 %) of the corresponding dioxalate, m.p. 160-163C. ;
Analysis for C14H22N209S:
Calc.: 42.53 % C 5.61 % H 7.08 % N
Found: 42.55 % C 5.76 C/o H 7.24 % N
-'' ' . : '
Claims (3)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of 2-[[[5-(dimethylamino)-methyl-2-furanyl] methy] thio] ethaneamine of the formula characterized in that in 2-[[[5-(dimethylamino)methyl-2-furanyl]
methyl] thio]ethanol of the formula the primary alcoholic hydroxy group is halogenated to give the halogenide of the formula wherein Hal is chlorine or bromine, and the resulting compound is aminated with ammonia to yield the desired compound.
methyl] thio]ethanol of the formula the primary alcoholic hydroxy group is halogenated to give the halogenide of the formula wherein Hal is chlorine or bromine, and the resulting compound is aminated with ammonia to yield the desired compound.
2. A process according to claim 1, characterized in that the primary alcoholic hydroxy group is halogenated with SOCl2 in methylene chloride at room temperature or with a solution of HBr in acetic acid.
3, A process according to claim 1, characterized in that the amination with ammonia is carried out at reflux temperature of the reaction mixture.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YUP2607/82 | 1982-11-22 | ||
| YU2607/82A YU42818B (en) | 1982-11-22 | 1982-11-22 | Process for preparing 2-///5-(dimethyl-amino)-methyl-2-furanyl/methyl/thio/ethaneamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177491A true CA1177491A (en) | 1984-11-06 |
Family
ID=25558385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000429776A Expired CA1177491A (en) | 1982-11-22 | 1983-06-06 | Process for the preparation of 2-¬¬¬5- (dimethylamino)methyl-2-furanylmethylthio furanyl|methyl|thio|ethaneamine ethaneamine |
Country Status (12)
| Country | Link |
|---|---|
| KR (1) | KR870000272B1 (en) |
| AT (1) | AT384217B (en) |
| CA (1) | CA1177491A (en) |
| CS (1) | CS235040B2 (en) |
| DD (1) | DD209829A5 (en) |
| ES (1) | ES8500926A1 (en) |
| FI (1) | FI832245L (en) |
| HU (1) | HU194848B (en) |
| PL (1) | PL242064A1 (en) |
| PT (1) | PT76759B (en) |
| SU (1) | SU1187719A3 (en) |
| YU (1) | YU42818B (en) |
-
1982
- 1982-11-22 YU YU2607/82A patent/YU42818B/en unknown
-
1983
- 1983-05-16 AT AT0177683A patent/AT384217B/en not_active IP Right Cessation
- 1983-05-19 PL PL24206483A patent/PL242064A1/en unknown
- 1983-05-19 CS CS833564A patent/CS235040B2/en unknown
- 1983-05-24 HU HU831826A patent/HU194848B/en unknown
- 1983-05-25 PT PT76759A patent/PT76759B/en unknown
- 1983-05-31 SU SU833600200A patent/SU1187719A3/en active
- 1983-06-06 CA CA000429776A patent/CA1177491A/en not_active Expired
- 1983-06-10 DD DD83251907A patent/DD209829A5/en unknown
- 1983-06-14 ES ES523236A patent/ES8500926A1/en not_active Expired
- 1983-06-20 FI FI832245A patent/FI832245L/en not_active Application Discontinuation
- 1983-06-20 KR KR1019830002759A patent/KR870000272B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU42818B (en) | 1988-12-31 |
| ATA177683A (en) | 1987-03-15 |
| KR840006637A (en) | 1984-12-01 |
| CS235040B2 (en) | 1985-04-16 |
| YU260782A (en) | 1984-10-31 |
| PT76759B (en) | 1986-01-14 |
| SU1187719A3 (en) | 1985-10-23 |
| ES523236A0 (en) | 1984-11-16 |
| KR870000272B1 (en) | 1987-02-23 |
| PL242064A1 (en) | 1984-07-30 |
| DD209829A5 (en) | 1984-05-23 |
| PT76759A (en) | 1983-06-01 |
| ES8500926A1 (en) | 1984-11-16 |
| HU194848B (en) | 1988-03-28 |
| AT384217B (en) | 1987-10-12 |
| FI832245A0 (en) | 1983-06-20 |
| FI832245L (en) | 1984-05-23 |
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| MKEC | Expiry (correction) | ||
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