ChemicalBook CAS DataBase List BUT-3-YN-1-AMINE

BUT-3-YN-1-AMINE synthesis

8synthesis methods

Product Name:BUT-3-YN-1-AMINE
CAS Number:14044-63-4
Molecular formula:C4H7N
Molecular Weight:69.11

14396-90-8
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14044-63-4
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Yield:-

Reaction Conditions:

with hydrazine in methanol at 20;

Steps:

1 SS-1-97B:
To a stirred solution of SS-1-95 (180 mg, 0.9 mmol) in MeOH (5 mL) was added N2H4 (0.06 mL, 1.13 mmol). The resulting mixture was stirred at room temperature for 16 h. Then participate was filtered off, and the filtrate was quenched with water (5 mL), and acidified to pH 2 with 2 N HC1. The solution was concentrated under vacuum to afford SS-1-97A as white powder. The crude product was used directly into the next step. To a stirred solution of SS-1-97A in DCM (5 mL) was added TEA (0.37 mL, 2.7 mmol) and benzoyl chloride (252 mg, 1.8 mmol) at 0 °C. Then the resulting mixture was stirred at the same temperature for 30 mm. The reaction was quenched with water (5 mL), and extracted with DCM (3 x 10 mL). The combined organic extracts were washed with brine (40 mL), dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by flash chromatography (0 - 50% EtOAc/Hexene), and the title compound was obtained as white powder (140 mg, 90%). ‘H NMR (400 IVIHz, Acetone-cl6) 7.93 (dd, J= 5.3, 3.2 Hz, 3H), 7.58 -7.53 (m, 1H), 7.49 (dd, J 8.1, 6.6 Hz, 2H), 3.57 (td, J= 7.1, 6.0 Hz, 2H), 2.55 (td, J 7.1, 2.7 Hz, 2H), 2.43 (t, J 2.7 Hz, 1H).

References:

THE GEORGE WASHINGTON UNIVERSITY;THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS;VILLAGRA, Alejandro;KOZIKOWSKI, Alan P.;SHEN, Sida WO2018/183701, 2018, A1 Location in patent:Paragraph 0244; 0248; 0252; 0256

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