Ammonia → 5-Pentafluoroethyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline

関与物質

役割	名称	HCID	仕込み量
反応物	Ammonia	HCID 222	—
反応物	Toluene	HCID 1140	—
反応物	Sodium pentafluoropropionate	HCID 2733305	—
反応物	1-(5-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone	HCID 18414274	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	5-Pentafluoroethyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline	HCID 18414282	66%

反応手順

A mixture of 5-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (4.0 g, 13 mmol), sodium pentafluoropropionate (4.85 g, 26 mmol), copper (I) iodide (5.22 g, 27.2 mmol), toluene (70 ml) and dimethylformamide (70 ml) was heated under argon with Dean-Stark distillation (70 ml distillate collected), then heated at reflux for 18 h. The mixture was cooled, then poured into a mixture of water (150 ml) and 0.880 ammonia (150 ml). Resulting solution was extracted with dichloromethane (4×100 ml) and the combined extracts dried (Na2SO4) and evaporated in vacuo to give a solid. Chromatography on silica with 10-50% ether-hexane gradient elution gave the title compound (2.97 g, 66%) as a colourless solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06465485B1
出典データセット	uspto-grants-2002_10
ORD ID	ord-ef4bc42f83794e03be0bdf36dd93c47d
出典メモ	uspto-grants-2002_10