Water → HCID 57315557, compound

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cyclopropylamine	HCID 69828	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 57315557	HCID 57315557	—

Reaction Steps

To a stirred solution of 1,1-dimethyl-3-butynoic acid (247 mg, 2.2 mmol), cyclopropylamine (0.23 mL, 3.3 mmol), HOBt.H2O (506 mg, 3.3 mmol) and i-Pr2NEt (1.2 mL, 6.6 mmol) in CH2Cl2 (10 mL) was added EDC.HCl (633 mg, 3.3 mmol). The mixture was stirred at rt for 18 h, diluted with ether (90 mL), washed with 5% aq HCl (15 mL) and satd aq NaHCO3 (15 mL), and dried over Na2SO4. Removal of the solvent left N-cyclopropyl-2,2-dimethylbut-3-ynamide (187 mg, 56%). 1H NMR (CDCl3) 0.53 (m, 2H), 0.79 (m, 2H), 1.44 (s, 6H), 2.45 (s, 1H), 2.73 (m, 1H), 6.76 (br s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883778B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-01336a93642d490ea8c2bb6f9777eaf7
Source note	uspto-grants-2014_11