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ChemicalBook CAS DataBase List 1-N-BOC-4-(3-BROMOPHENYL)-4-CYANOPIPERIDINE

1-N-BOC-4-(3-BROMOPHENYL)-4-CYANOPIPERIDINE synthesis

2synthesis methods
31938-07-5 Synthesis
3-Bromophenylacetonitrile

31938-07-5
234 suppliers
$8.00/5g

118753-70-1 Synthesis
Tert-butyl bis(2-chloroethyl)carbamate

118753-70-1
176 suppliers
$6.00/1g

1-N-BOC-4-(3-BROMOPHENYL)-4-CYANOPIPERIDINE

849928-28-5
24 suppliers
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Yield:849928-28-5 63%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 60; for 17 h;

Steps:

4.2.5 General synthesis of compounds 8a-8g

General procedure: To a solution of 7 (1.66mmol) and substituted benzeneacetonitrile (1.66mmol) in anhydrous DMF (5mL) was added NaH (60% dispersion in mineral oil, 8.4mmol) portion wise at 0°C over 1h. The reaction mixture was heated at 60°C for 16h. The reaction mixture was poured into ice-water (50mL) and extracted with ethyl acetate (3×50mL). The combined organic layers were washed with brine (2×50mL), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography eluting with ether/ethyl ether (15:1) to give 8a-8g.

References:

Liu, Yang;Yin, Yanzhen;Zhang, Zhen;Li, Carrie J.;Zhang, Hui;Zhang, Daoguang;Jiang, Changying;Nomie, Krystle;Zhang, Liang;Wang, Michael L.;Zhao, Guisen [European Journal of Medicinal Chemistry,2017,vol. 138,p. 543 - 551]

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