* 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.
at 90℃; for 3 h; Inert atmosphere; Green chemistry
General procedure: Under an inert atmosphere, a mixture containing the ionic liquid (1–6) (0.1 g), amine (0.55mmol), and butyl chloride (0.5mmol)was heated at 90 °C for 3 h. The reaction mixture was then diluted with aqueous NaHCO3 and extracted with Et2O. The combined organic layers were dried with anhydrous MgSO4, and the solvent was removed in vacuum.The crude mixture was analyzed by GC–MS and NMR spectroscopy.
93 %Chromat.
With tetrabutylammomium bromide; sodium hydroxide In water at 100℃; for 2 h;
General procedure: SiO2-CuI (0.1 g,5 molpercent Cu) was added to a mixture of amine (0.5 mmol), benzyl chloride, allyl bromide, or n-butyl chloride (0.5 mmol for N-substitution and 1 mmol for N,N-disubstitution), NaOH (2 mmol), and TBAB (0.25 mmol) in a round-bottom flask(25 mL) in water (4mL). The reaction mixture was stirred at 15°C (in the case of N-benzylation, allylation, or alkylation of primary amines,Table 2) or 70–100°C (in the case of N,N-dibenzylation, allylation, or alkylation of primary amines, Table 3), and 100°C(N-benzylation, allylation, and alkylation of secondary amines, Table 4) for an appropriate time. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was triturated with EtOAc (20 mL) and the SiO2-CuI was filtered off. The product was obtained after removal of the solvent under reduced pressure followed by column chromatography or crystallization from EtOAc–petroleum ether.
Reference：
[1] Journal of Molecular Liquids, 2015, vol. 204, p. 210 - 215
[2] Synthetic Communications, 2014, vol. 44, # 5, p. 620 - 632
2
[ 110-91-8 ]
[ 123-72-8 ]
[ 1005-67-0 ]
Reference：
[1] Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2195 - 2199
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 3073
3
[ 110-91-8 ]
[ 109-74-0 ]
[ 1005-67-0 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 293 - 304
4
[ 110-91-8 ]
[ 109-74-0 ]
[ 1005-67-0 ]
[ 111-92-2 ]
Yield
Reaction Conditions
Operation in experiment
75 %Chromat.
at 120℃; Flow reactor
General procedure: A reduced moist catalyst was loaded into the reactor and dried in a hydrogen stream at 120° just before the reaction. The reaction was performed in a plug flow reactor at atmospheric pressure and temperature 100–240°C. The laboratory-scale reactor was a 12Kh18N10T steel pipe of inner diameter 9 mm placed in an electric oven with heating zone height 50 mm. The reactor temperature was monitored using a thermocouple. The hydrogen feeding was controlled using a GV-7 hydrogen generator. A mixture of the corresponding catalyst, nitrile, and amine was loaded into the reactor and heated at 100–240°C under hydrogen flow. The reaction course was monitored by means of chromato-mass spectrometry.
Reference：
[1] Russian Journal of General Chemistry, 2017, vol. 87, # 11, p. 2546 - 2551[2] Zh. Obshch. Khim., 2017, vol. 87, # 11, p. 1804 - 1809,6
5
[ 110-91-8 ]
[ 109-74-0 ]
[ 1005-67-0 ]
[ 102-82-9 ]
[ 111-92-2 ]
Yield
Reaction Conditions
Operation in experiment
45 %Chromat.
at 120℃; Flow reactor
General procedure: A reduced moist catalyst was loaded into the reactor and dried in a hydrogen stream at 120° just before the reaction. The reaction was performed in a plug flow reactor at atmospheric pressure and temperature 100–240°C. The laboratory-scale reactor was a 12Kh18N10T steel pipe of inner diameter 9 mm placed in an electric oven with heating zone height 50 mm. The reactor temperature was monitored using a thermocouple. The hydrogen feeding was controlled using a GV-7 hydrogen generator. A mixture of the corresponding catalyst, nitrile, and amine was loaded into the reactor and heated at 100–240°C under hydrogen flow. The reaction course was monitored by means of chromato-mass spectrometry. Reductive amination of butyronitrile 1a. a. Nitrile : amine : hydrogen ratio 1 : 1 : 15, catalyst Ni0/C, reaction temperature 120°C, feeding rate of a mixture of butyronitrile 1a and morpholine 2a 3.6 mL h–1 gcat–1, hydrogen feeding rate 6 L h–1 gcat–1. Nitrile 1a conversion 93percent. Yield: 45percent of N-n-butylmorpholine 3a, 31percent of di-n-butylamine 4a, and 15percent of tri-n-butylamine 5a. N-n-Butylmorpholine (3a). Mass spectrum, m/e (Irel, percent): 143.9 (10) [M + 1], 142.7 (3) [M], 99.9 (100), 70.0 (16). Di-n-butylamine (4a). Mass spectrum, m/e (Irel, percent): 130.8 (2) [M + 2], 129.8 (15) [M + 1], 128.6 (2) [M], 99.8 (8), 85.8 (100), 70 (15), 56.9 (33), 44.1 (20), 43.0 (20), 41.1 (34). Tri-n-butylamine (5a). Mass spectrum, m/e (Irel, percent): 184.0 (2), 141.8 (100), 99.9 (75), 58.0 (55), 44.0 (11), 41.0 (8).
Reference：
[1] Russian Journal of General Chemistry, 2017, vol. 87, # 11, p. 2546 - 2551[2] Zh. Obshch. Khim., 2017, vol. 87, # 11, p. 1804 - 1809,6
6
[ 110-91-8 ]
[ 109-65-9 ]
[ 1005-67-0 ]
Reference：
[1] Synthetic Communications, 2009, vol. 39, # 13, p. 2297 - 2303
[2] Synthesis, 1985, # 3, p. 282 - 285
[3] Journal of the American Chemical Society, 1939, vol. 61, p. 771
[4] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 3285,3288; engl. Ausg. S. 3310, 3312
7
[ 93627-55-5 ]
[ 1005-67-0 ]
Reference：
[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 1, p. 5 - 11
8
[ 110-91-8 ]
[ 542-69-8 ]
[ 1005-67-0 ]
Reference：
[1] Journal of the American Chemical Society, 1939, vol. 61, p. 771
[2] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 3285,3288; engl. Ausg. S. 3310, 3312
9
[ 111-46-6 ]
[ 1005-67-0 ]
Reference：
[1] Journal of the American Chemical Society, 1950, vol. 72, p. 1597
10
[ 111-75-1 ]
[ 1005-67-0 ]
Reference：
[1] Yakugaku Zasshi, 1954, vol. 74, p. 1162,1164[2] Chem.Abstr., 1955, p. 14767
[3] DRP/DRBP Org.Chem.,
11
[ 110-91-8 ]
[ 71-36-3 ]
[ 1005-67-0 ]
Reference：
[1] Yakugaku Zasshi, 1954, vol. 74, p. 1162,1164[2] Chem.Abstr., 1955, p. 14767
12
[ 109-65-9 ]
[ 1005-67-0 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 365 - 368[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 406 - 409
13
[ 542-69-8 ]
[ 1005-67-0 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 365 - 368[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 406 - 409
14
[ 1708-29-8 ]
[ 109-73-9 ]
[ 1005-67-0 ]
Reference：
[1] Synthesis, 1985, # 6/7, p. 701 - 703
Example 10 A solution of 3.06 g (21.7 mmol) of (1,N)-(but-2-enyl)-morpholine, 0.023 g (0.024 mmol) of HRuCl(CO)(PPh3)3 and 0.034 g (0.125 mmol) of triphenylphosphine was admixed with 20 g of water and the mixture was stirred at 12 bar of hydrogen and 150 C. Following a reaction period of 20 h there was obtained a yield of 90% at a selectivity of 64 percent by area of 1-butanol, 4 percent by area of (1,N)-(but-1-enyl)morpholine and 32 percent of <strong>[1005-67-0]N-butylmorpholine</strong>, as determined by gaschromatographic anaylsis. The morpholine was recovered.
With C11H19N2O2(1+)*Cl(1-); at 90℃; for 3.0h;Inert atmosphere; Green chemistry;
General procedure: Under an inert atmosphere, a mixture containing the ionic liquid (1-6) (0.1 g), amine (0.55mmol), and butyl chloride (0.5mmol)was heated at 90 C for 3 h. The reaction mixture was then diluted with aqueous NaHCO3 and extracted with Et2O. The combined organic layers were dried with anhydrous MgSO4, and the solvent was removed in vacuum.The crude mixture was analyzed by GC-MS and NMR spectroscopy.
93%Chromat.
With tetrabutylammomium bromide; sodium hydroxide; In water; at 100℃; for 2.0h;
General procedure: SiO2-CuI (0.1 g,5 mol% Cu) was added to a mixture of amine (0.5 mmol), benzyl chloride, allyl bromide, or n-butyl chloride (0.5 mmol for N-substitution and 1 mmol for N,N-disubstitution), NaOH (2 mmol), and TBAB (0.25 mmol) in a round-bottom flask(25 mL) in water (4mL). The reaction mixture was stirred at 15C (in the case of N-benzylation, allylation, or alkylation of primary amines,Table 2) or 70-100C (in the case of N,N-dibenzylation, allylation, or alkylation of primary amines, Table 3), and 100C(N-benzylation, allylation, and alkylation of secondary amines, Table 4) for an appropriate time. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was triturated with EtOAc (20 mL) and the SiO2-CuI was filtered off. The product was obtained after removal of the solvent under reduced pressure followed by column chromatography or crystallization from EtOAc-petroleum ether.
N-butyl-N-methylmorpholinium bis(fluorosulfonyl)imide salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
In tetrachloromethane; at 80℃; for 15.0h;Inert atmosphere;
In 500mL flask were added 189g of carbontetrachloride, (171.8g, 1.2mol) <strong>[1005-67-0]N-butylmorpholine</strong>, (195g, 1.0mol) N-methyl-bis(sulfonylfluoride)amine, in a nitrogen atmosphere, heated to 80C, the reaction was stirred for 15 hours. Stand for cooling, at a temperature of 200 C, a pressure of 5.0Pa conditions distillation under reduced pressure to remove excess reactants, colorless liquid was collected and washed repeatedly with 50ml of ethyl acetate three times, and then at a temperature of 90 C, vacuum degree under conditions of 0.01MPa and dried in vacuo to give a colorless liquid N-butyl N-methylmorpholinium bis(fluorosulfonyl)imide salt, yield 89%.
With hydrogen; at 120℃; under 760.051 Torr;Flow reactor;
General procedure: A reduced moist catalyst was loaded into the reactor and dried in a hydrogen stream at 120 just before the reaction. The reaction was performed in a plug flow reactor at atmospheric pressure and temperature 100-240C. The laboratory-scale reactor was a 12Kh18N10T steel pipe of inner diameter 9 mm placed in an electric oven with heating zone height 50 mm. The reactor temperature was monitored using a thermocouple. The hydrogen feeding was controlled using a GV-7 hydrogen generator. A mixture of the corresponding catalyst, nitrile, and amine was loaded into the reactor and heated at 100-240C under hydrogen flow. The reaction course was monitored by means of chromato-mass spectrometry.
With hydrogen; at 120℃; under 760.051 Torr;Flow reactor;
General procedure: A reduced moist catalyst was loaded into the reactor and dried in a hydrogen stream at 120 just before the reaction. The reaction was performed in a plug flow reactor at atmospheric pressure and temperature 100-240C. The laboratory-scale reactor was a 12Kh18N10T steel pipe of inner diameter 9 mm placed in an electric oven with heating zone height 50 mm. The reactor temperature was monitored using a thermocouple. The hydrogen feeding was controlled using a GV-7 hydrogen generator. A mixture of the corresponding catalyst, nitrile, and amine was loaded into the reactor and heated at 100-240C under hydrogen flow. The reaction course was monitored by means of chromato-mass spectrometry. Reductive amination of butyronitrile 1a. a. Nitrile : amine : hydrogen ratio 1 : 1 : 15, catalyst Ni0/C, reaction temperature 120C, feeding rate of a mixture of butyronitrile 1a and morpholine 2a 3.6 mL h-1 gcat-1, hydrogen feeding rate 6 L h-1 gcat-1. Nitrile 1a conversion 93%. Yield: 45% of N-n-butylmorpholine 3a, 31% of di-n-butylamine 4a, and 15% of tri-n-butylamine 5a. N-n-Butylmorpholine (3a). Mass spectrum, m/e (Irel, %): 143.9 (10) [M + 1], 142.7 (3) [M], 99.9 (100), 70.0 (16). Di-n-butylamine (4a). Mass spectrum, m/e (Irel, %): 130.8 (2) [M + 2], 129.8 (15) [M + 1], 128.6 (2) [M], 99.8 (8), 85.8 (100), 70 (15), 56.9 (33), 44.1 (20), 43.0 (20), 41.1 (34). Tri-n-butylamine (5a). Mass spectrum, m/e (Irel, %): 184.0 (2), 141.8 (100), 99.9 (75), 58.0 (55), 44.0 (11), 41.0 (8).
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