3-BUTYN-1-AMINE HYDROCHLORIDE

Preparation 18; iV-But-3-ynyl-2, 2-dimethyl-ρropionamide; But-3-ynyl amine hydrochloride: Dissolve but-3-ynyl-carbamic acid tert-butyl ester (1.81 g, 0.1 mmol) in DCM (5 mL) and add 5N aqueous HCl (5 mL). Stir vigorously at room temperature overnight. Concentrate in vacuo to a minimum amount of volume and then freeze dry to obtain the desired material as a white solid (809 mg, 79percent).iV-But-3-ynyl-2, 2-dimethγl-propionamide:; Add triethylamine (3 mL) to a suspension of but-3-ynylamine hydrochloride (200 mg, 2.1 mmol) in DCM (10 mL) and stir for 10 min at room temperature under nitrogen. Add then neat pivaloyl chloride (284.9 μL, 2.31 mmol) and stir at room temperature overnight under nitrogen. Concentrate in vacuo, take up the residue in methanol and filter through a SCX-2 cartridge eluting with methanol to obtain the title compound (265 mg, 65percent).5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide (DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 °C and stirred for 3.5 h, cooled to 25 °C and extracted with Et5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide(DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 °C and stirredfor 3.5 h, cooled to 25 °C and extracted with Et2O (50 mL 3 3). The combined organic phase was washed with water, brine, and dried over Na2SO4. Volatile solvents were removed by rotary evaporation. The resulting residue containing3-butyn-1-azide was used without further purification and was mixed with triphenyl phosphine (6.44 g, 24.4 mmol) inEt2O (100 mL) at 0° C and stirred for 2 h. Water (3.9 mL) was added and the resulting mixture stirred for an additional20 h at 25 °C. The mixture was poured into 1N HCl (25 mL) and the aqueous layer extracted with Et2O (10 mL 3 3).The remaining aqueous layer was concentrated under reduced pressure rotary evaporation to give 1.25 g 3-butyn-1-aminium chloride (49 percent yield for two steps

Molecular Weight:105.56
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:105.0345270
Monoisotopic Mass:105.0345270
Topological Polar Surface Area:26
Heavy Atom Count:6
Complexity:47.9
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes