Category: 935-44-4

Synthetic Route of 935-44-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 935-44-4 name is 1-Phenyl-1-cyclopropanecarbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Methylmagnesium bromide (3.0 M in tetrahydrofuran, 3.0 mL, 9.0 mmol) was added to a solution of 1-phenyl-1-cyclopropanecarbonitrile (429 mg, 3.0 mmol) in anhydrous tetrahydrofuran (4 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated to 100 C. for 10 minutes in a microwave oven. Then titanium(IV) isopropoxide (0.9 mL, 3.0 mmol) was added and the reaction mixture was heated to 50 C. for 1 hour in the microwave. After cooling, a solution of 25% aqueous ammonia (2 mL) was added dropwise to the reaction mixture. The suspension was filtered through a Celite pad which was washed with tetrahydrofuran. The combined filtrate was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-(1-phenylcyclopropyl)propan-2-amine (400 mg) as a crude yellow oil: MS m/z: 178 (M+1).The crude amine (200 mg, 1.1 mmol) was combined with compound 1 (100 mg, 0.27 mmol) and potassium carbonate (150 mg, 1.1 mmol) in dioxane (20 mL) and heated to reflux overnight. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were dried with anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by reversed phase flash chromatography (0 to 85% acetonitrile in 0.01% ammonium bicarbonate) to give compound A30 (46 mg 34% yield) as a white solid: 94.4% purity (HPLC); MS m/z: 506.2 (M+1); 1H NMR (CDCl3, 500 MHz) delta 8.34 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.5 Hz, 1H), 7.61 (t, JHF=54.0 Hz, 1H), 7.42 (m, 2H), 7.35 (m, 2H), 7.29 (m, 2H), 7.24 (m, 1H), 5.26 (s, 1H), 4.00-3.65 (m, 8H), 1.48 (s, 6H), 1.17 (m, 2H), 0.84 (m, 2H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyl-1-cyclopropanecarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Pathway Therapeutics Inc.; US2012/252802; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 935-44-4, name is 1-Phenyl-1-cyclopropanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H9N

INTERMEDIATE 45 4-(1-Cyanocyclopropyl)benzenesulfonyl chloride To a solution of 1-phenylcyclopropanecarbonitrile (0.5 g, 3.5 mmol) in 5 mL of chloroform was added 0.5 mL of ClSO3H at 0 C. After stirring at rt stirred overnight, the reaction mixture was poured into ice-water (50 mL) and the product was extracted with CHCl3 (75 mL). The extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated to give the title compound. 1H NMR (500 MHz, CD3OD): delta 8.08 (2H, d), 7.77 (2H, d), 1.60 (2H, t), 1.21 (2H, t).

The synthetic route of 935-44-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; EP2102201; (2010); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts