3-Bromobenzonitrile → HCID 68831348, compound

Participants

Role	Name	HCID	Charge
Reactant	3-Bromobenzonitrile	HCID 23381	—
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	HCID 68829062	HCID 68829062	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 68831348	HCID 68831348	81.2%

Reaction Conditions

Temperature	110 °C

Reaction Steps

4-(2-Benzyloxy-4-methoxyphenyl)-pyrrolidin-2-one (2.0 g. 6.8 mmol), potassium phosphate (2.56 g, 1.8 eq), and 3-bromobenzonitrile (1.82 g, 1.5 eq) was added to a flask under N2. The mixture was charged with 10 mL DMF and 10 mL dioxane followed by the addition of 1,2-trans-cyclohexanediamine (100 μL) and CuI (180 mg). The mixture was heated at 110° C. for 20 h and cooled down to r.t. Next the mixture was diluted with 150 mL EtOAc, washed with sat. NH4Cl, water, and brine, and then dried. After concentration, the residue was purified on silica gel (EtOAc: Hexane=3:1) to give 2.2 g of the desired product. Yield: 81%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07495016B2
Source dataset	uspto-grants-2009_02
ORD ID	ord-6c108a28afed48d6891793f7e21ff866
Source note	uspto-grants-2009_02