* 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.
Reference：
[1] Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 7, p. 1484 - 1497
[2] Patent: US4695575, 1987, A,
[3] Tetrahedron, 2008, vol. 64, # 10, p. 2456 - 2464
2
[ 105-58-8 ]
[ 65214-82-6 ]
Yield
Reaction Conditions
Operation in experiment
58.7 mg
at 150℃; for 6 h;
2. In a 500 mL pressure-resistant reactor, 295.3 g (2.50 mol) of diethyl carbonate was added to 86.7 g (0.50 mol) of the product obtained in the previous step, the closed system was heated to 150° C., and the reaction was incubated for 6 hours. The remaining GC raw material was <1. percent, the reaction is completed, the temperature is lowered, diethyl carbonate is distilled off under reduced pressure, the residue is dissolved in ethyl acetate, and 1M hydrochloric acid is added dropwise to adjust the pH to 1-2, stirred for 0.5 hours, and the layers are separated and the aqueous layer is extracted with ethyl acetate once. The layers are combined and decompressed to concentrate the solvent and distilled under reduced pressure to obtain a pale yellow oil product.N-ethoxycarbonyl-4-hydroxypiperidine 58.7 g, yield 67.8percent in two-step reaction,GC content 98.3percent,
Reference：
[1] Patent: CN107827810, 2018, A, . Location in patent: Paragraph 0018; 0020; 0023; 0026
3
[ 5382-16-1 ]
[ 541-41-3 ]
[ 65214-82-6 ]
Reference：
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4118 - 4134
ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.5 parts (31.5%)
In N,N-dimethyl-formamide;
EXAMPLE 20 To a stirred mixture of 3.5 parts of ethyl 4-hydroxy-1-piperidinecarboxylate and 135 parts of N,N-dimethylformamide was added 1 part of a sodium hydride dispersion 50% and stirring was continued for 2 hours at room temperature. After the addition of 5.2 parts of 2-chloro-1-[(4-fluorophenyl)methyl]-1H-benzimidazole, the whole was further stirred overnight at room temperature. The reaction mixture was poured into ice water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 2.5 parts (31.5%) of ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate; mp. 94.0 C. (26).
Ethoxycarbonyl-4-piperidinol(According to the addition amount of N-ethoxycarbonyl-4-piperidinol, as the first to fifthGroup, the specific amount of added and the amount of added substances in Table 1) N-ethoxycarbonyl-4-piperidinol added to 500 ml four bottles,Join300 ml of toluene,3 g of 98percent concentrated sulfuric acid, and then 60 g (0.273 mol)? - (4-chlorophenyl) -2-pyridinemethanol,The reaction was heated to reflux (temperature 112 ° C), and the reaction was continued at that temperature for 7 hours. After completion of the TLC monitoring, the reaction was stopped and the reaction was stoppedThe organic phase was washed with 100 ml of water * 2 and the organic phase was concentrated under reduced pressure to give 4 - [(4-chlorophenyl) (2-pyridyl) methoxy]1-carboxylic acid ethyl ester as an oil which was used in the next step without further purification.
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