Acetyl chloride → 1-(7-acetyl-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Participants

Role	Name	HCID	Charge
Reactant	Acetyl chloride	HCID 6367	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Aluminum(III) Chloride	HCID 6451240	—
Reactant	2,2,2-Trifluoro-1-(1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)ethan-1-one	HCID 21864732	—
Solvent	1,2-Dichloroethane	HCID 11	—
Product	1-(7-acetyl-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone	HCID 21864704	—

Reaction Steps

1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (253 mg, 1.0 mmol) and AcCl (0.68 mL, 10 mmol) were dissolved in DCE (3 mL) and treated with aluminum chloride (AlCl3) (667 mg, 5.0 mmol). The resulting yellow mixture was stirred for 30 minutes then poured over ice and saturated aqueous NaHCO3 solution. After stirring 20 minutes the mixture was extracted with CH2Cl2 (3×30 mL). The organic layer was dried through a cotton plug then concentrated to a orange-yellow oil (255 mg, 86%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06605610B1
Source dataset	uspto-grants-2003_08
ORD ID	ord-bfea9390f7584f24a401da01fc3aa938
Source note	uspto-grants-2003_08