4-Butylmorpholine

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.General procedure: SiOGeneral 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.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 NiGeneral 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 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.In 500mL flask were added 189g of carbontetrachloride, (171.8g, 1.2mol) 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.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.

< 25,000 lb

Molecular Weight:143.23
XLogP3:1.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:143.131014166
Monoisotopic Mass:143.131014166
Topological Polar Surface Area:12.5
Heavy Atom Count:10
Complexity:79.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes