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[ CAS No. 73889-19-7 ]

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Chemical Structure| 73889-19-7
Chemical Structure| 73889-19-7
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Product Details of [ 73889-19-7 ]

CAS No. :73889-19-7MDL No. :MFCD03093979
Formula :C17H26N2O2Boiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :290.40Pubchem ID :4438618
Synonyms :

Computed Properties of [ 73889-19-7 ]

TPSA : 41.6 H-Bond Acceptor Count : 3
XLogP3 : 3 H-Bond Donor Count : 1
SP3 : 0.59 Rotatable Bond Count : 5

Safety of [ 73889-19-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73889-19-7 ]

  • Upstream synthesis route of [ 73889-19-7 ]
  • Downstream synthetic route of [ 73889-19-7 ]

[ 73889-19-7 ] Synthesis Path-Upstream   1~8

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  • [ 24424-99-5 ]
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YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 20℃; To a solution of l-benzylpiperidin-4-amine (1 mL, 933 mg, 4.9 mmol) in dry DCM (20 mL) were added Et3N (1 mL, 725 mg, 7.2 mmol) and di-tert-butyl dicarbonate (1.23 g, 5.6 mmol). The reaction mixture was stirred overnight at room temperature and then diluted with DCM (20 mL). The organic layer was washed with aqueous NaHC03 solution (10 mL) and brine (10 mL), dried over anhydrous MgS04 and concentrated in vacuo to give tert-butyl (1- benzylpiperidin-4-yl)carbamate (1.42 g, quant.) as a white solid.
96% at 0 - 20℃; for 72.00 h; To a solution of l-benzyl-4-amiopiperidine (57.1 g) in methylene chloride (300 mL) was added tert-butyl dicarboxylare (68.8 g) under ice-cooling and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and to the residue was added ethyl acetate and an aqueous sodium hydrogencarbonate solution. The mixture was stirred and the organic layer was washed with a brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude crystals were washed with diisopropylether and collected by filtration. The filtrate was concentrated in vacuo and the resultant crude crystals were washed with diisopropylether and collected by filtration. The crude crystals were combined and dried to obtain l-benzyl-4- (tert-butoxycarbonyl)aminopiperidine (83.2 g, yield: 96 percent) as a pale yellow solid. MS(APCI)m/z; 291 [M+H]+
93% With sodium hydroxide In water; <i>tert</i>-butyl alcohol at 0 - 20℃; 1-Benzyl-piperidin-4-ylamine (50 g, 262.76 mmol) is dissolved in a mixture of 200 ml of water, 145 ml of 2 molar aqueous sodium hydroxide and 350 mi of t-BuOH at 0°C. A solution of Boc20 (63.1 g, 1.1 equivalents) in 150 ml of t-BuOH is added dropwise within one hour at 0°C. A white suspension is formed which is allowed to stir overnight at room temperature. The reaction mixture is diluted with ether and washed with water, . The organic layers are dried over anhydrous sodium sulfate and evaporated under reduced pressure. Yield: 71.5 g of a pale yellow solid (93percent). MS (ESI) : 291 [M+H] +, 1 H-NMR (DMSO-d6) : 5 (ppm) 7.2-7. 35 (m, 5H), 6.77 (br d, 1 H), 3.44 (s, 2H), 3.22 (br m, 1 H), 2.75 (m, 2H), 1.95 (dt, 2H), 1.68 (m, 2H), 1.38 (s, 9H), 1.36 (dt 2H).
82.8% With sodium hydroxide In water; <i>tert</i>-butyl alcohol at 20℃; for 12.00 h; l-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol), the starting material, was dissolved in IM aqueous sodium hydroxide solution (35.8 ml) and t- butanol(32 ml) in a 250 ml vessel, and /-butyl-dicarbonate ((^-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring, and the resulting mixture was20 reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. Then, the organic layer was washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was purified with a silica gel column 5 chromatography to obtain 3.80 g of the title compound as a white solid (82.8percent). EPO <DP n="35"/>1H-NMR (200 MHz, CDCl3) δ 1.38 (s, 9H), 1.86-2.33 (m, 4H), 2.70 (m, 2H), 3.40 (m, 2H), 3.57 (br, IH), 4.12 (s, 2H), 7.43 (m, 3H), 7.55 (m, 2H). LCZMS (M+H): 291; Preparation of f-butyl-l- benzylpiperidin-4-ylcarbamate (the compound of formula 12) l-Benzylpiperidin-4-ylamine (3g, 15.8 mmol) was dissolved in IM EPO <DP n="78"/>aqueous sodium hydroxide solution (35.8 ml) and ^-butanol (32 ml) in a 250 ml vessel, and /-butyl-dicarbonate ((^-Boc^O; 3.79 g, 17.38 mmol) was added thereto while stirring. The resulting mixture was reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (yield 82.8percent).1H-NMR (200 MHz, CDCl3) δ 1.38 (s, 9H), 1.86-2.33 (m, 4H), 2.70 (m, 2H), 3.40 (m, 2H), 3.57 (br, IH), 4.12 (s, 2H), 7.43 (m, 3H), 7.55 (m, 2H).LCZMS (M+H): 291; l-Benzylpiperidin-4-ylamine (3 g, 15.8 mmol) as a starting material was dissolved in IM aqueous sodium hydroxide solution (35.8 ml) and t- butanol (32 ml) in a 250 ml vessel, and r-butyl-dicarbonate ((.pound.-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring. The resulting mixture was reacted at room temperature for 12 hrs. After the completion of reaction, the reaction mixture was extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid aqueous solution and brine in order, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 3.801 g of the title compound as a white solid (82.8percent).1H-NMR (200 MHz, CDCl3) δ 1.38 (s, 9H), 1.86-2.33 (m, 4H), 2.70 (m, 2H), 3.40 (m, 2H), 3.57 (br, IH), 4.12 (s, 2H), 7.43 (m, 3H), 7.55 (m, 2H). LCMS (M+H): 291.
82.8% With sodium hydroxide In water; <i>tert</i>-butyl alcohol for 12.00 h; l-Benzylpiperidine-4-amine (3g, 15.8mml), the starting material, was dissolved in IM aqueous sodium hydroxide solution (35.8 ml) and t-butanol (32 ml) in the 250 ml reaction vessel, ?-butyl dicarbonate ((?-Boc)2O; 3.79 g, 17.38 mmol) was added thereto while stirring, and the mixture was reacted for 12 hrs. After the completion of the reaction, the reaction mixture was extracted with ethyl ether 2 times. The extract was washed with 0.1N hydrochloric acid solution and salt water in order. The resulting organic layer <n="19"/>was dried over anhydrous sodium sulfate, filtered, concentrated under a reduced pressure and then subjected to silica gel column chromatography to obtain 3.80 g of the title compound as a white solid (yield: 82.8percent).1H -NMR (200 MHz, CDCl3) δ 1.38 (s, 9H), 1.86-2.33 (m, 4H)5 2.70 (m, 2H), 3.40 (m, 2H), 3.57 (br, IH)5 4.12 (s, 2H), 7.43 (m, 3H), 7.55 (m, 2H). LC/MS (M+H): 291
22.2 mmol, 90.3% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran EXAMPLE 5
1-Benzyl-4-(tert-butoxycarbonylamino)piperidine (79)
4-Amino-1-benzylpiperidine (5.0 mL, 24.6 mmol) tetrahydrofuran (70 mL), and diisopropylethylamine (10.3 mL, 59.1 mmol) were combined under Ar and cooled in an ice bath. Di-tert-butyl dicarbonate (6.45 g, 29.6 mmol) in tetrahydrofuran (30 mL) was added dropwise.
The reaction solution was allowed to warm to room temperature and stirred 24 h.
The solvent was removed in vacuo and the remaining residue was purified by flash column chromatography (hexane:ethyl acetate 70:30) to give a solid.
Trituration with ether gave 6.44 g (22.2 mmol, 90.3percent) of Compound 79 as a solid.
1H NMR (CDCl3, 300 MHz) δ 7.30-7.26 (m, 5H), 4.45-4.35 (s, br, 1H), 3.48 (s, 3H), 2.85-2.75 (m, 2H), 2.15-2.05 (m, 2H), 1.95-1.85 (m, 2H), 1.44 (s, 11H).
0.99% With sodium hydrogencarbonate In water for 4.00 h; 2.00 g of 4-amino-1-benzylpiperidine was added to a 100-mL round-bottomed flask, and then 20.0 mL of deionized water and 20.0 mL of saturated sodium hydrogen carbonate (NaHCO3) were added thereto. After 2.41 g of di-tert-butyl dicarbamate (Boc2O) was added thereto, the reaction mixture was vigorously stirred for about 4 hours and then concentrated under reduced pressure. The aqueous phase was extracted with 20.0 mL of ethyl acetate (EtOAc) obtain an organic phase. The organic phase was washed with 15.0 mL of deionized water and 5.00 mL of saturated brine. The organic phase was filtered with sodium sulfate (Na2SO4). The resulting filtrate was distilled under reduced pressure. As a result, 3.04 g of tert-butyl (1-benzylpiperidine-4-yl)carbamate was obtained with a yield of about 99.7percent. (0257) 3.04 g of tert-butyl (1-benzylpiperidine-4-yl)carbamate was added to a 100-mL round-bottomed flask, and then 45.0 mL of tetrahydrofuran was added thereto. After 2.50 g of lithium aluminum hydride (LiAlH4) was added thereto, the reaction mixture was refluxed for about 4 hour and then cooled at room temperature. 4.50 mL of deionized water was slowly added thereto while cooling. After the reaction mixture was stirred for about 5 minutes, 4.50 mL of a 15percent sodium hydroxide (NaOH) aqueous solution was added thereto. The reaction mixture was further stirred for about 5 minutes, and then 13.5 mL of deionized water was added thereto to terminate the reaction. The reaction mixture was filtered through a Celite™ 545 filter agent. The resulting filtrate was distilled under reduced pressure. As a result, 2.22 g of 1-benzyl-N-methylpiperidine-4-amine was obtained with a quantitative yield. (0258) 1.00 g of 1-benzyl-N-methylpiperidine-4-amine was added to a 50-mL round-bottomed flask, and then 20.0 mL of deionized water was added thereto. After 790 mg of 6-chloro-7-deazapurine was added thereto, 1.35 g of potassium carbonate (K2CO3) was added into the reaction mixture. The reaction mixture was refluxed for about 24 hours and then cooled at room temperature. The reaction mixture was then extracted three times with 10.0 mL of dichloromethane (CH2Cl2) to collect an organic phase. The collected organic phase was concentrated under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). As a result, 607 mg of N-(1-benzylpiperidine-4-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 38.7percent. (0259) 350 mg of N-(1-benzylpiperidine-4-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 50-mL round-bottomed flask, and then dissolved with 7.00 mL of methanol and 1.00 mL of dichloromethane (CH2Cl2). After 350 mg of a 10w/wpercent palladium/ carbon (Pd/C) was added thereto, a hydrogen-containing balloon was installed on the reaction flask. The reaction mixture was vigorously stirred for about 24 hours and then filtered through a Celite™ 545 filter agent. The resulting filtrate was concentrated under reduced pressure. The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 220 mg of N-methyl-N-(piperidine-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 87.7percent. (0260) 150 mg of N-methyl-N-(piperidine-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 5-mL round-bottomed flask and then dissolved with 1.50 mL of n-butanol. After 0.690 mL of ethyl cyanoacetate was added into the solution, the reaction mixture was treated with 0.0485 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then heated at about 80°C for about 24 hours. After termination of the reaction, the reaction solution was distilled under reduced pressure to remove the solvent. The resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 6.20 mg of 3-(4-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)piperidine-1-yl)-3-oxopropanenitrile was obtained with a yield of about 3.20percent. (0261) 1H NMR (400 MHz, DMSO) δ12.65 (s, 1H), 8.38 (s, 1H), 7.43 (s, 1H), 6.90 (d, J = 1.6 Hz, 1H), 4.75 (s, 1H), 4.52 (d, J = 12.8 Hz, 1H), 4.08 (s, 2H), 3.81 (d, J = 13.6 Hz, 1H), 3.27-3.20 (m, 3H), 2.82-2.75 (m, 1H), 2.03-1.91 (m, 1H), 1.77 (s, 2H), 1.23-1.18 (m, 2H). (0262) LRMS (ESI) calcd for (C15H18N6O + H+) 299.2, found 299.1.

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