Dichloromethane → Ammonia dichloromethane

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Diethylethanolamine	HCID 7497	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Di-tert-butyl diazene-1,2-dicarboxylate	HCID 6034084	—
Reactant	4-Piperidin-1-yl methyl-phenol	HCID 20035992	—
Product	Diethyl-[2-(4-piperidin-1-yl methyl-phenoxy)-ethyl]-amine	HCID 17962621	—
Product	Ammonia dichloromethane	HCID 22731429	3%

Reaction Steps

A suspension of the product of Example 17 (176 mg), 2-Diethylamino-ethanol (0.12 mL), and polymer supported triphenylphosphine (613 mg; loading: 3 mmol/g) in DCM (5 mL) was treated with di-tert-butylazodicarboxylate (316 mg). After 2 h, the resulting mixture was filtered, and the filtrate was evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a pale yellow oil (37 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.8 Hz, 2H), 6.84 (d, J=8.6 Hz, 2H), 4.03 (t, J=6.5 Hz, 2H), 3.40 (s, 2H), 2.87 (t, J=6.5 Hz, 2H), 2.63 (q, J=7.0 Hz, 4H), 2.35 (br s, 4H), 1.59–1.52 (m, 4H), 1.46–1.37 (m, 2H), 1.07 (t, J=7.1 Hz, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07186732B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-f2d6ec256b704a95a2991abf985b0bc9
Source note	uspto-grants-2007_03