Water → Depyrazine 7,8-Dinitrophenyl Varenicline

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Dichloromethane methanol	HCID 21226129	—
Reactant	1-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one	HCID 21864744	—
Solvent	Methanol	HCID 887	—
Product	Depyrazine 7,8-Dinitrophenyl Varenicline	HCID 9878181	—

Reaction Steps

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-triflouroethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL)) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration. the residue was chromatographed to provide brown solids. (1.9 g. 71%). (TLC 5% MeOH/CH2Cl2 (NH3) Rf0.36). 1H NMR (400 MHz, CDCl3) δ7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H). GCMS m/e 249 (M+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06410550B1
Source dataset	uspto-grants-2002_06
ORD ID	ord-c8abf7582ecb4b2ab0b8467e63cc20e6
Source note	uspto-grants-2002_06