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CAS No. : | 87571-88-8 | MDL No. : | MFCD00215843 |
Formula : | C8H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HJGMRAKQWLKWMH-IEESLHIDSA-N |
M.W : | 140.23 | Pubchem ID : | 736442 |
Synonyms : |
|
Signal Word: | Danger | Class: | 3,8 |
Precautionary Statements: | P210-P240-P241-P242-P243-P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P403+P235-P405-P501 | UN#: | 2733 |
Hazard Statements: | H226-H335-H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; ammonium formate; In methanol; water; | Compound 1a (8.8 g, 0.04 mol) was dissolved in a mixture of methanol (115 mL) and H2O (13 mL). Subsequently, HCOONH4 (26.0 g, 0.4 mol) and 10% Pd/C (5.2 g) were added and the mixture was stirred for 24 h. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was treated with 30% aqueous solution of NaOH (20 mL) and stirred for 5 min. The mixture was extracted with diethyl ether (5 × 30 mL) and the combined organic layers were dried with magnesium sulphate and evaporated in vacuo. The residue was subjected to distillation. Yield: 2.0 g (22.3%). Bp 112-120 C/0.6 Tr; Mp (hydrochloride) > 310 C, dec.; Anal. Calcd for C12H21N2O × 2HCl: C 50.89%, H 8.54%, N 9.89%; Found: C 50.89%, H 8.20%, N 9.86%; IR (KBr) cm-1 nu 3357 (NHas), 3298 (NHsym), 1067 (CO); 1H NMR (400 MHz, CDCl3): delta 3.85 (C10H, 1H, m), 3.77 (C13H(1), 1H, q, 2J = 3J = 7.5 Hz), 3.65 (C13H(2), 1H, q), 3.20 (C1H, 1H, ps), 3.10 (C5H, 1H, ps), 3.12 (C3H, 1H, m), 2.38 (C9H(1), 1H, dd, 2J = 13 Hz, 3J = 7 Hz), 2.31 (C9H(2), 1H, dd, 2J = 13 Hz, 3J = 4.5 Hz), 2.06 (C2H, C4Heq, 2H, m), 1.90 (C11H(1), 1H, m), 1.88 (C6H, C7Hax, C6H, C7Heq, 4H, pd), 1.76 (C12H, 2H, m), 1.45 (C11H(2), 1H, m), 1,30 (C2H, C4Hax, 2H, pd), 1.23 (NH2, 2H, bs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With triethylamine; In dichloromethane; toluene; | EXAMPLE 9 endo-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-5-chloroindole-1-carboxamide (E9) STR42 To phosgene [3.8 ml (12.5% w/w solution in toluene)] in dry dichloromethane (50 ml) was added dropwise 2,3-dihydro-5-chloroindole (D4) (0.83 g) in CH2 Cl2 (20 ml). Triethylamine (0.83 ml) was then added and the whole stirred at room temperature for 10 min. endo-3-Amino-8-methyl-8-azabicyclo[3.2.1]octane (0.83 g) in dry dichloromethane (10 ml) was added and the reaction mixture stirred at room temperature for 2 h, then washed with saturated potassium bicarbonate solution (15 ml) and brine (20 ml). The organic phase was dried (Na2 SO4), the solvent evaporated in vacuo and the residue column chromatographed on alumina eluding with chloroform to give, after crystallisation from ethyl acetate, the title compound (E9) (0.36 g, 19%) m.p. 149-50. 1 H-NMR (CDCl3) 400 MHz: delta 7.81 (d, 1H), 7.15-7.05 (m, 2H), 4.90 (bd, 1H), 4.08 (q, 1H), 3.91 (t, 2H), 3.28-3.10 (m, 4H), 2.34 (s, 3H), 2.35-2.08 (m, 4H), 1.90-1.65 (m, 4H). |
With triethylamine; In CH2l2; dichloromethane; toluene; | Example 9 endo-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-5-chloroindole-1-carboxamide (E9) To phosgene [3.8ml (12.5% w/w solution in toluene)] in dry dichloromethane (50ml) was added dropwise 2,3-dihydro-5-chloroindole (D4) (0.83g) in CH2l2(20ml). triethylamine (0.83ml) was then added and the whole stirred at room temperature for 10 min. endo-3-Amino-8-methyl-8-azabicyclo[3.2.1]octane (0.83g) in dry dichloromethane (10ml) was added and the reaction mixture stirred at room temperature for 2h, then washed with saturated potassium bicarbonate solution (15ml) and brine (20ml). The organic phase was dried (Na2O4, the solvent evaporated in vacuo and the residue column chromatographed on alumina eluding with chloroform to give, after crystallisation from ethyl acetate, the title compound (E9) (0.36g, 19%) m.p. 149-50o 1-NMR (CDCl3 400MHz delta 7.81 (d, 1H). 7.15-7.05 (m, 2H). 4.90 (bd, 1H). 4.08 (q, 1H). 3.91 (t, 2H). 3.28-3.10 (m, 4H). 2.34 (s, 3H). 2.35-2.08 (m, 4H). 1.90-1.65 (m, 4H) m, 4H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; dichloromethane; | EXAMPLE 3 endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-methyl-alpha-oxo-3-indoleacetamide The following is the Preparation of a compound of Formula I in which X and Y are hydrogen; R1 is Formula (d); Z is --N(CH3)--; and R3 is endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl. 1-methyl-alpha-oxo-3-indoleacetyl chloride (1.0 g; 4.8 mmol) in 40 ml of methylene chloride was mixed with 40 ml of methylene chloride containing endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane (675 mg; 4.8 mmoles). The reaction mixture was stirred at ambient temperature for 16 hours and at reflux temperature for an additional 4 hours. The mixture was allowed to cool to ambient temperature and then mixed with a solution of saturated sodium bicarbonate and stirred form 30 minutes. The organic phase was separated, dried over potassium carbonate, filtered and concentrated. The resulting product was dissolved in 5 to 10 ml of hot ethanol and acidified with hydrogen chloride (200 mg) in 2 ml of ethanol. The solution was cooled and the product crystallized to yield 1.38 g (3.8 mmol) of endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-methyl-alpha-oxo-3-indoleacetamide hydrochloride, m.p. 308-310 C. Proceeding as in Example 3 but replacing endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane with |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; water; | (1) endo-4-Acetylamino-5-chloro-2-methoxy-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)benzamide To a mixture of 38.0 g of 4-acetylamino-5-chloro-2-methoxybenzoic acid, 26.1 ml of triethylamine, and 500 ml of tetrahydrofuran, 15.7 ml of ethyl chloroformate was added dropwise with stirring under ice-cooling. Stirring was continued for 1 hour under ice-cooling, and then a solution of 23.0 g of endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine in 40 ml of tetrahydrofuran was added dropwise. Stirring was continued for 1.5 hours at room temperature, and then insoluble materials were removed and the filtrate obtained was concentrated under reduced pressure. Water was added to the residue and pH was adjusted to 9 by using aqueous potassium carbonate solution. Crystals precipitated were collected by filtration and Washed with water and then with ethyl acetate to give 48.6 g of slightly yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-carbonyldiimidazole; In chloroform; N,N-dimethyl-formamide; | EXAMPLE 9 8-Fluoro-N-(endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-propyl-1,4-dihydro-4-oxocinnoline-3-carboxamide hydrochloride (Compound No.102 in Table 1) To a solution of 1.0 g 8-fluoro-1-propyl-1,4-dihydro-4-oxocinnoline-3-carboxylic acid in 10 ml N,N-dimethylformamide was added 0.78 g N,N'-carbonyldiimidazole at room temperature and the mixture stirred for 30 min to obtain a solution of imidazolideo To the solution was added dropwise a solution of 0.62 g endo-8-methyl-8-azabicyclo[3.2.1]octane-3-amine in 2 ml N,N-dimethylformamide at room temperature and the mixture stirred for another 6 hr. The reaction mixture was evaporated to remove the solvent and the residue was dissolved in chloroform and extracted with aqueous 3N HCl solution. The aqueous solution was made basic with sodium hydrogen carbonate and extracted with chloroform. The organic layer was taken, dried with sodium sulfate and evaporated to remove the solvent. The residue was recrystallized from chloroform/ethyl acetate to give the titled compound in the free form. It was treated with 1N hydrochloric acid ethanol solution to yield 1.04 g of the desired compound. M.p.=290-292 C. (decomp.) 1 H-NMR(CDCl3, delta ppm) 1.02 (3H,t), 1.90-2.10 (2H,m), 2.10-2.26 (2H,m), 2.28-2.66 (4H,m), 2.81 (3H,m), 3.02-3.32 (2H,m), 3.83 (2H,bs), 4.44-4.58 (1H,m), 4.64-4.84 (2H,m), 7.48-7.70 (2H,m), 8.22-8.36 (1H,m), 10.54 (1H,d) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In thionyl chloride; ethyl acetate; benzene; | Reference Example 12 Preparation of endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide The title compound corresponding to Compound (7), wherein X is imino, was prepared as the intermediate according to Preparation Scheme I. A solution of 0.5 g of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid in 5 ml of thionyl chloride was stirred to reflux for 2 hours. After thionyl chloride was thoroughly distilled off under vacuum, 3 ml of benzene was added to the residue. Under ice cooling a solution of 0.36 g of endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane in 3 ml of benzene was dropwise added to the benzene solution of the acid chloride described above. The mixture was stirred at room temperature for 2 hours. After ethyl acetate was added thereto, the organic layer was washed with water and then with saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under vacuum. The resulting residue was purified by alumina column chromatography (chloroform) to give 390 mg of endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide. mp: 175.8-177.8 C. (ethyl acetate) MS (m/z); 353 (M+), 214, 172, 84. IR nu (cm-1, Neat); 3263, 1673, 1528, 1206. NMR (ppm, CDCl3); 1.68 (6H, d, J=7.2 Hz), 1.76 (1H, s), 1.83 (1H, s), 2.00-2.40 (6H, m), 2.34 (3H, s), 3.10-3.28 (2H, m), 4.30 (1H, q, J=7.2 Hz), 5.40-5.90 (1H, m), 7.22-7.33 (1H, m), 7.55-7.70 (2H, m), 7.75 (1H, d, J=7.8 Hz), 8.83 (1H, s), 10.48 (1H, d, J=7.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3(c) Preparation of (endo)-N-(8-methyl-8-azabicyclo[3.2. l]oct-3-yl)guanidine hydrochloride; Prepared as described in example 3(a) with the addition of 1 mole equivalent of HCl to the diethyl ether quench prior to stirring.M.p. = 240-244 C; 300 MHz 1H NMR (DMSO-d6) delta: 10.98 (br. s, 1H), 8.31 (d, J= 6.3Hz, 1H), 7.51 (br. s, 3H), 3.76 (m, 3H), 2.6 (m, 5H), 2.4 (m, 2H), 2.2 (m, 2H), 1.85 (d, J = 15.4 Hz, 2H); LCMS: 183 [M+H]. CaIc. for C9H18N4 2 HCl: C 42.32, H 7.90, N 21.95; found C 39.78, H 7.91, N 22.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With ammonia; sodium hydrogencarbonate; triethylamine; In methanol; dichloromethane; water; ethyl acetate; | EXAMPLE I N-(endo-8-methyl-8-azabicyclo[3,2,1]oct-3-yl)-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-carboxamide 0.75 g (3.7 mmol) of 7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-carboxylic acid and 0.52 g (3.7 mmol) of endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane and 1.14 g (4.5 mmol) of 2-chloro-1-methyl-pyridinium iodide and 0.9 g (9 mmol) of triethylamine were brought into 30 ml of methylene chloride and the mixture was boiled for 1 hour while stirring. The mixture was then cooled and shaken two times with a 5% solution of sodium bicarbonate in water. The methylene chloride layer was evaporated in vacuum and the residue was chromatographed over silica gel using methylene chloride/methanol/ammonia in the ratio 84/15/1 as an eluent. The desired fraction was evaporated in vacuum. The residue was dissolved in ethyl acetate. 1.1 Equivalent of alcoholic hydrochloric acid were added, the solid was sucked off, washed with ethyl acetate and dried. Yield: 1.1 g (82%); melting-point: 285 C. (decomposition) STR16 1H NMR (400 MHz, CDCl3; ref. TMS) In an analogous manner N-(endo-9-methyl-9-azabicyclo[3,3,1]-non-3-yl]-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-carboxamide was obtained as an amorphous substance. Yield: 60% 1 H NMR (400 MHz, CDCl3; ref TMS) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; N,N-dimethyl-formamide; | EXAMPLE 3 (Endo)-N-(8-methyl-8-azabicyclo[3.2.1] octan-3-yl)-1-benzyl-1,4-dihydro-4-oxoquinoline-3-carboxamide 1-Benzyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.96 g, 7.03 mmol) in dry DMF (20 ml) was treated with carbonyl diimidazole (1.14 g, 7.04 mmol) at room temperature and the mixture heated at 80 C. for 3 hours. (Endo)-3- aminotropane (0.99 g, 7.07 mmol) was added and heating continued overnight (19 hours) to give a suspension. The mixture was diluted with water (40 ml) and the pH adjusted to 9-10 by addition of concentrated aqueous potassium carbonate. The solid was collected, washed well with water, dried and recrystallized from ethanol (20 ml) and water (20 ml) to give the product free base (1.72 g). This was dissolved in boiling ethanol (15 ml) and the solution acidified with ethanolic hydrogen chloride. The resulting precipitate was collected, washed with ethanol and dried at 80 C. in vacuo to give the title compound as the hydrochloride, hydrate, one-third ethanolate (1.91 g), mp 296 to 297 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethanol; dichloromethane; water; | EXAMPLE 8 (Endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-4-oxo-1-n-propylquinoline-3-carboxamide 1,4-Dihydro-4-oxo-1-n-propylquinoline-3-carboxylic acid (1.58 g, 6.82 mmol) and triethylamine (0.7 g, 7 mmol) were dissolved in dichloromethane (20 ml), under an Argon blanket. Diphenylphosphinic chloride (1.6 g, 6.76 mmol) were added all at once with stirring. The solution was left for 6 h then (endo)-3-aminotropane (1.0 g, 7.14 mmol) and triethlamine (0.7 g, 7 mmol) were added. The solution was left for 3 days, then evaporated. The residue was dissolved in water and acidified with concentrated hydrochloric acid. The precipitate was filtered off, washed with water and discarded. The filtrate was basified with sodium carbonate and evaporated. The residue was triturated twice with ethyl acetate, the ethyl acetate evaporated, and the residue triturated with water (6 ml) and concentrated ammonia (1 ml) to give a white solid (1.34 g). This material (3.68 mmol) was dissolved in hot ethanol (15 ml) and oxalic acid dihydrate (0.47 g, 3.73 mmol) was added. The resulting solution was refrigerated overnight. The precipitate was collected, washed with ethanol and dried to give the title compound as the oxalate, half hydrate (1.24 g), m.p. 227-231. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In N-methyl-acetamide; ethanol; water; | EXAMPLE 2 (Endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-1-butyl-4-oxoquinoline-3-carboxamide A mixture of 1-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.98 g, 4 mmol), carbonyldimidazole (0.07 g, 4.4 mmol) and dimethylformamide (12 ml) was stirred at 80 C. for 1.5 hours. (Endo)-3-aminotropane (0.56 g, 4 mmol) was then added and stirring continued for a further 1.5 hours at the same temperature. The solvent was removed and the residue diluted with ice-water (15 g). The precipitated solid was collected, washed with ice-cold water and air dried. The base was dissolved in a hot mixture of water (5 ml) and ethanol (3 ml), then ice-cooled and basified to pH 11 by addition of concentrated aqueous ammonia to precipitate the crystalline product which was collected and washed with cold dilute ammonia solution. The purified base (0.82 g) was then dissolved in ethanol (8 ml), acidified with ethanolic HCl and diluted with ether (3 ml). Ice-cooling gave the product as the hydrochloride (0.49 g) mp. 267-268 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(o) From 4-chlorocarbonyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane, endo-4,9-dihydro-3-methyl-4-[(8-methyl-8-azabicyclo[3,2,1]oct-3-yl)amino]carbonyl}-10H-thieno]3,4-b][1,5]benzodiazepin-10-one was obtained; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | EXAMPLE 6 endo-5,10-Dihydro-5-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one The above compound was prepared analogously to Example 1 from 5-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane, in a yield of 58% of theory. Colorless crystals, m.p.: 264-266 C. (acetonitrile). C22 H24 N4 O2 (376.46): Calculated: C 70.19; H 6.43; N 14.88. Found: C 79.90; H 6.53; N 14.94. IR (CH2 Cl2): NH 3450/cm, 3370/cm, CO 1660 and 1675/cm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(b) From 4,9-dihydro-4-chlorocarbonyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane, endo-4,9-dihydro-4-[(8-methyl-8-azabicyclo[3,2,1]-oct-3-yl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained, m.p. 203-205 C. (acetonitrile); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(n) From 4-chlorocarbonyl-4,9-dihydro-1-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane, endo-4,9-dihydro-1-methyl-4-[(8-methyl-8-azabicyclo[3,2,1]oct-3-yl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(p) From 4-chlorocarbonyl-4,9-dihydro-1,3-dimethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane, endo-4,9-dihydro-1,3-dimethyl-4-[(8-methyl-8-azabicyclo[3,2,1]oct-3-yl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(q) From 3-chloro-4-chlorocarbonyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and endo-3-amino-8-methyl-8-azabicyclo[3,2,1]octane, endo-3-chloro-4,9-dihydro-4-[(8-methyl-8-azabicyclo[3,2,1]oct-3-yl)amino]carbonyl}-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained, m.p. 158-161 C. (acetonitrile); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
palladium-carbon; In ethanol; | EXAMPLE 31 (endo)-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-N'-(5-hydroxy-2-methoxyphenyl)urea monohydrochloride (E31) STR46 The 5-benzyloxy-2-methoxyphenyl isocyanate and (endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine were converted via the procedure outlined in Example 1 to (endo)-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-N'-(5-benzyloxy-2-methoxyphenyl)urea which was converted to the monohydrochloride salt. The hydrochloride salt was hydrogenated at atmospheric pressure and room temperature over 10% Pd/C in ethanol to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine; In hydrogenchloride; diethyl ether; dichloromethane; | EXAMPLE 19 (endo)-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-2-methylindole-1-carboxamide hydrochloride (E19) STR52 To 1-(2,3-dihydro-2-methyl)indolylcarbonyl chloride (D18) (0.5 g) in dry dichloromethane (50 ml) was added dropwise a mixture of (endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (0.36 g) and triethylamine (0.36 ml) in dry dichloromethane (25 ml). The reaction mixture was stirred at ambient temperature overnight, the solvent was then evaporated under reduced pressure. The residue was dissolved in 5N hydrochloric acid solution (20 ml) and was washed with diethyl ether (50 ml). The aqueous phase was basified with potassium carbonate and then the product was extracted into dichloromethane (3*50 ml). The organic phase was dried (Na2 SO4), the solvent was evaporated under reduced pressure and the residue filtered through a short alumina column eluding with 25% dichloromethane/75% chloroform. The product was isolated as the hydrochloride salt from ethyl alcohol and diethyl ether to give the title compound (E19) (0.64 g, 78%) mp 292-3 C. 1 H-NMR (d6 -DMSO) 270 MHz: delta10.38 (bs, 1H), 7.78 (d, 1H), 7.18 (d, 1H), 7.08 (t, 1H), 6.85 (t, 1H), 6.30 (bs, 1H), 4.85-4.70 (m, 1H), 3.90-3.65 (m, 3H), 3.32 (s, 3H), 2.85-2.00 (m, 10H), 1.15 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; | EXAMPLE 2 (endo)-N-(8-Methyl-8-azabicyclo[3,2,1]oct-3-yl)-N'-(3-methoxy-pyrid-2-yl)urea (E2) STR13 A solution of <strong>[10201-71-5]2-amino-3-methoxypyridine</strong> (0.55 g) and 1,1'-carbonyldiimidazole (0.86 g) in xylene (50 ml) was stirred at room temperature for 1 h. A solution of (endo)-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (0.8 g) in xylene (10 ml) was added and the whole heated to reflux for 2 h. The reaction mixture was evaporated to dryness and the residue partitioned between CHCl3 (100 ml) and saturated NaHCO3 solution (50 ml). The CHCl3 extract was removed, dried (K2 CO3) and evaporated to dryness. The residue was purified by column chromatography (Al2 O3, CH2 Cl2 -CHCl3), to give the title compound (0.9 g) m.p. 178-80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; toluene; | EXAMPLE 1 (endo)-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-N'-(2-methoxy-pyrid-3-yl)urea (E1) STR12 To a stirred solution of phosgene (12.5% in toluene, 7.3 ml), in CH2 Cl2 (80 ml) at room temperature was added 3-amino-2-methoxypyridine (1.0 g) in CH2 Cl2 (5 ml). After stirring the reaction mixture for 10 min., triethylamine (2.5 ml) was added and the stirring continued for a further 10 mins. A solution of (endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (1.13 g) in CH2 Cl2 (5 ml) was then added and the whole stirred for 3 h. The solution was washed with sat. NaHCO3 solution, dried (K2 CO3) and evaporated to dryness. Purification of the residue by column chromatography (T.L.C. grade alumina, CH2 Cl2) afforded the title compound (E1) (1.3 g) m.p. 197-200 C. (CH2 Cl2 /Et2 O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; ethyl acetate; toluene; | EXAMPLE 32 (Endo)-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-N'-(2-methoxycarbonylphenyl)urea (E32) STR47 A solution of phosgene in toluene (12.5%, 7.5 ml) was added to a stirred solution of methyl anthranilate (1.2 g) in dry CH2 Cl2 (100 ml) at 0 C. After 10 min, triethylamine (2.5 ml) was added. After a further 10 min, a solution of (endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (1.12 g) in CH2 Cl2 (10 ml) was added and the reaction stirred to room temperature for 4 h. The reaction mixture was then washed with excess sat. NaHCO3 solution, dried (K2 CO3) and concentrated in vacuo. Recrystallisation of the residue from ethyl acetate/petrol gave the title compound (E32) (1.8 g) m.p. 125-7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | EXAMPLE 2 (endo)-N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-ethylindolizin-1-carboxamide (E2) STR16 A solution of 3-ethylindolizin-1-carboxylic acid (1.0 g) in CH2 Cl2 (100 ml) at 0 C. was treated with oxalyl chloride (0.46 ml). After stirring for 1h, a solution of (endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (0.75 g) and triethylamine (1.0 g) in CH2 Cl2 (20 ml) was added and the whole stirred at room temperature for 2h. The reaction mixture was washed with saturated NaHCO3 solution (2*50 ml), dried (K2 CO3) and concentrated. The residue was crystallized from ethyl acetate/petrol to give the title compound (1.0 g). m.p. 182-3 C. 1 H-Nmr (CDCl3) delta: 8.33 (d, 1H), 7.78 (d, 1H), 6.95 (d,d,d, 1H), 6.70 (t, 1H), 6.60 (s, 1H), 6.18 (brd, 1H), 4.32 (q, 1H) 3.20 (brs, 2H, 2.82 (q, 2H), 2.40-2.10 (m, 7H including 2.32, s, 3H), 1.95-1.75 (m, 4H), 1.40 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | EXAMPLE 1 Preparation of endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane STR7 A solution of O-methyl-8-methyl-8-azabicyclo[3.2.1]octan-3-one oxime(500 g; 3 moles) in methanol (3.2 L) and 0.88 ammonia (1.8 L. 9. equivs) was hydrogenated over 5% rhodium on carbon paste (50 g dry wt.) at 35-50 psi (241.3-344.8 kPa) and 50 C. for 16 hours. After cooling and purging with nitrogen, the catalyst was filtered off and washed with fresh methanol (2*500 ml). The solvent was distilled out and the residue diluted with isopropanol (1.5 L). The solvent was again distilled out to leave the title compound as an oil which was distilled (bp 86/7 mm) to give the purified title compound as a colourless solid (344 g, 82%). 1 H NMR (CDCl3, JEOL 270 MHz): delta3.2 (t,1H), delta3.1 (m,2H), delta2.25 (s,3H), delta2.1 (m,2H), delta2.0 (m,4H) delta1.45 (dd,2H). 13 C NMR (CDCl3; JEOL 67.8 MHz): delta26.2 (CH2); delta39.4 (CH2); delta40.4 (CH or CH3); delta42.7 (CH or CH3); delta60.3 (CH or CH3) Mass Spec. (JEOL DX303) El: m/z 140 (M+), 124, 96, 83. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; | (a) (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,2,2-trichloroacetamide hydrochloride. endo-3-Amino-8-methyl-8-azabicyclo[3.2.1]octane (7.0 g, 50 mmol) in chloroform (25 ml) was treated with hexachloroacetone (15.885 g, 60 mmol) in chloroform (35 ml). The mixture was heated to reflux for 5 [1/2 ] h. Further hexachloroacetone (3.5 g, 13.2 mmol) was added and the mixture was heated again for 3 h. On cooling, several crops of the crude title compound salt were obtained by concentration of the reaction mixture. The residual oil was then diluted to 50 ml with propan-2-ol and treated with excess ethereal HCl. The precipitated crude hydrochloride was recrystallized from propan-2-ol-methanol and then from ethylacetate-methanol giving the title compound as almost colourless crystals (7.42 g) subliming and decomposing without melting above 220. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With triethylamine; In 1,4-dioxane; water; at 20℃; for 16h; | STEP 1 : To a 5 L round-bottom flask was added 8-methyl-8- azabicyclo[3.2.1]octan-3-endo-amine (432 g, 3.1 mol), 2 L of dry 1 ,4-dioxane, 675 mL of deionized water and 468 g of dry triethylamine. Di-tert-butyl dicarbonate (solution in 1.2 L of dioxane) was added dropwise to the stirring solution at room temperature over 16 h. The reaction mixture was concentrated and the resulting residue suspended in 2.5 L of methylene chloride, then washed twice with 1 L of water, dried with anhydrous magnesium sulfate, filtered, and volatile organics removed by rotary evaporation to yield 617 g (83%) of tert-butyl 8-methyl-8- azabicyclo[3.2.1]octan-3-ylcarbamate (mp 79-81 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In 1,4-dioxane; water; at 20℃; for 16h; | To a 5 L round-bottom flask was added 8-methyl-8-azabicyclo[3.2.1]octan-3-endo-amine (432 g, 3.1 mol), 2 L of dry 1,4-dioxane, 675 mL of deionized water and 468 g of dry triethylamine. Di-tert-butyl dicarbonate (solution in 1.2 L of dioxane) was added dropwise to the stirring solution at room temperature over 16 h. The reaction mixture was concentrated and the resulting residue suspended in 2.5 L of methylene chloride. then washed twice with 1 L of water, dried with anhydrous magnesium sulfate, filtered, and volatile organics removed by rotary evaporation to yield 617 g (83%) of tert-butyl 8-methyl-8-azabicyclo[3.2.1]octan-3-ylcarbamate (mp 79-81 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; at 20℃;Cooling with ice; | After dissolving 8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine (CAS87571-88-8) (2.00 g) and pyridine (1.62 ml) in tetrahydrofuran (30 ml), 2-fluorobenzoyl chloride (2.24 ml) was added dropwise while stirring on ice. The mixture was stirred at room temperature for 9 hours, and then an aqueous solution of potassium carbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (2.77 g).1H-NMR (400 MHz, CDCl3); delta 1.72-1.92 (m, 4H), 2.12-2.21 (m, 2H), 2.26-2.34 (m, 2H), 2.31 (s, 3H), 3.14-3.25 (m, 2H), 4.29-4.36 (m, 1H), 7.09-7.16 (m, 1H), 7.24-7.35 (m, 2H), 7.44-7.51 (m, 1H), 8.09-8.15 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | EXAMPLE 1; [0061] Synthesis of Benztropinamines (2a-m) - General Method.; The appropriate benzhydrol was dissolved in 10 ml SOCl2, at 0 0C, under an atmosphere of argon. The reaction mixture was warmed to reflux and allowed to stir at this temperature for 2-18 h. The reaction flask was cooled in an ice bath and the volatiles were removed in vacuo. Addition of EPO <DP n="23"/>dry toluene (2 x 5 ml) and removal in vacuo ensured the complete removal of SOCl2. The resulting viscous oil was determined spectroscopically to be the desired benzhydryl chloride. The resulting benzhydrylchloride (1.1 eq.) was added to the appropriate 3-aminotropane and NaHCO3 (2.5 eq) in acetonitrile and allowed to stir at reflux for 16 h. Upon completion of the reaction the volatiles were removed in vacuo, and the residue was purified by flash chromatography followed by cystallization of the appropriate salt.; Compound 2a. Prepared from 3alpha-aminotropane (see Berdini et al., Tetrahedron, 58, 5669 (2002)) and 4,4'-difluorobenhydryl chloride according to the general procedure. Yield: 71%. M.p. (oxalate, ethanol/diethyl ether) 166 0C. Rf 0.26 (chloroform/methanol 10:1, 1% ammonium hydroxide). IR (film): v 3303. 1H NMR (400 MHz, CDCl3): delta 1.57 (d, J 13.2, 2H), 1.96-2.05 (m, 6H), 2.25 (s, 3H), 2.74 (t, J 6.6, IH), 3.09 (s, 2H), 4.85 (s, IH), 6.93-6.97 (m, 4H), 7.18-7.22 (m, 4H). 13C NMR (101 MHz, CDCl3): delta 26.97, 37.05, 40.92, 46.92, 60.84, 63.29, 115.31 (JCF 21), 128.91 (JCF 8), 139.67 (JCF 3), 161.44 (JCF 243). Anal. (C2iH24F2N2-2(COOH)2-H2O) C, H, N. |
Tags: 87571-88-8 synthesis path| 87571-88-8 SDS| 87571-88-8 COA| 87571-88-8 purity| 87571-88-8 application| 87571-88-8 NMR| 87571-88-8 COA| 87571-88-8 structure
A1445185[ 2222100-22-1 ]
rel-(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine hydrochloride
Reason: Free-salt
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