4-Iodoaniline → 1-[4-(4-Amino-phenyl)-but-3-ynyl]-4-benzyl-piperidin-4-ol

Participants

Role	Name	HCID	Charge
Reactant	4-Iodoaniline	HCID 10893	—
Reactant	4-Benzyl-1-(3-butynyl)-4-hydroxypiperidine	HCID 10681704	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Triethylamine	HCID 8471	—
Product	1-[4-(4-Amino-phenyl)-but-3-ynyl]-4-benzyl-piperidin-4-ol	HCID 10616737	30%

Reaction Steps

A mixture of 4-benzyl-1-(but-3-yn-1-yl)-4-hydroxypiperidine (243 mg, 1.00 mmol), 4-iodoaniline (219 mg, 1.00 mmol), copper(I) iodide (40 mg), PdCl2(PPh3)2 (50 mg, 0.04 mmol) in 10 mL of Et3N is stirred at room temperature under N2 for 20 hr. The mixture is filtered and washed with Et3N (3×15 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a brown oil (100 mg, 30%): 1H NMR (CDCl3) 1.49 (m, 3 H), 1.72 (m, 2 H), 2.38 (m, 2 H), 2.55-2.66 (m, 6 H), 2.74 (s, 2 H), 3.75 (s, 2 H), 6.52 (d, J=8.4 Hz, 2 H), 7.15-7.30 (m, 7 H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06448270B1
Source dataset	uspto-grants-2002_09
ORD ID	ord-adf27a6516f3435aaa4f95c508a66fec
Source note	uspto-grants-2002_09