p-Fluoronitrobenzene → 1-Methyl-4-(4-nitrophenyl)-1,4-diazepane

Participants

Role	Name	HCID	Charge
Reactant	p-Fluoronitrobenzene	HCID 9590	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methylhomopiperazine	HCID 228349	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-Methyl-4-(4-nitrophenyl)-1,4-diazepane	HCID 3124722	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

The mixture of 1 -fluoro-4-nitrobenzene (880 mg, 6.2 mmol), 1-methylhomopiperazine (2.3 mL, 18.6 mmol), Cs2CO3 (6.1 g, 18.6 mmol) in 20 mL DMF was stirred at 100° C. for 1.5 hr. It was diluted with DCM, filtered to remove the inorganic salts, washed with water, dried, evaporated in vacuuo to afford 1-(4-nitrophenyl)-4-methylhomopiperazine in quantitative yield. ES-MS: (M+H)+236.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06632815B2
Source dataset	uspto-grants-2003_10
ORD ID	ord-477b6a04ce3c4bb1b3299c5aaabbffd5
Source note	uspto-grants-2003_10