ChemicalBook CAS DataBase List 3-(4-Chlorbutyl)-1H-indol-5-carbonitril

3-(4-Chlorbutyl)-1H-indol-5-carbonitril synthesis

8synthesis methods

Product Name:3-(4-Chlorbutyl)-1H-indol-5-carbonitril
CAS Number:143612-79-7
Molecular formula:C13H13ClN2
Molecular Weight:232.71

3-(4-Chlorbutyl)-1H-indol-5-carbonitril is an intermediate in the synthesis of vilazodone, mainly in laboratory development. It can be synthesized by acylation and reduction of 5-cyanoindole and 4-chlorobutyryl chloride.

6940-78-9 Synthesis

6940-78-9
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$5.00/10g

15861-24-2
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$10.00/5g

143612-79-7
332 suppliers
$23.00/1g

Yield:143612-79-7 88%

Reaction Conditions:

with zinc(II) chloride in dichloromethane at -10 - 5; for 2 h;Temperature;

Steps:

1-4 The preparation of 3- (4-chlorobutyl) indole-5-carbonitrile (Compound I) is as follows
Compound 1 (142.2g, 1.0mol) was dissolved in dichloromethane (1.5L), the internal temperature was controlled at 0-5 ° C, and anhydrous zinc chloride (150g, 1.1mol) was added.After the addition was completed, the temperature was lowered to about -10 ° C, and 1-bromo-4-chlorobutane (Compound 3) (188.6g, 1.1mol) was added dropwise.After the dropwise addition was completed, the temperature was raised to a reaction temperature of 0 ° C and the reaction was conducted for 2 hours.After the reaction was completed, dichloromethane (0.5 L) was diluted, and ice water (1 L) was destroyed. Subsequently, 1 N sodium hydroxide solution was added to neutralize to adjust pH = 7, and extraction and liquid separation were performed.The organic phase was washed with saturated brine (0.5 L) and separated.After the organic phase was concentrated to dryness, the residue was recrystallized from isopropyl acetate (0.5 L),205 g of the product (I) was obtained, the yield was 88%, and the HPLC purity was 99.62%.

References:

Shanghai Institute of Technology;Fang Yahui;Li Huixia CN111087340, 2020, A Location in patent:Paragraph 0039-0043; 0044-0047