N-(4-Fluorophenyl)-4-methylbenzylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-phenyl)-N-(4-methyl-benzyl)-acetamide

Participants

Role	Name	HCID	Charge
Reactant	N-(4-Fluorophenyl)-4-methylbenzylamine	HCID 292877	—
Reactant	(Z)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetyl chloride	HCID 12147055	—
Product	2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-phenyl)-N-(4-methyl-benzyl)-acetamide	HCID 69771503	—

Reaction Steps

Acylation of (4-fluorophenyl)-(4-methylbenzyl)-amine (Pombrik, S. I. et al., Izv. Akad. Nauk. SSSR Ser. Khim., 10, 1981, 2406-2408) with (Z)-2,2-dimethyl-5-(chlorocarbonylmethylene)-1,3-dioxolan-4-one as described in the preparation of Intermediate 71A gave the title amide as a syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.72 (6H, s, CH3), 2.31 (3H, s, CH3) 4.87 (2H, s, NCH2), 5.63 (1H, s, CH), 6.93-7.11 (8H, m, aromatics). HRMS (MAB N2) calculated for C21H20FNO4 [M−]: 369.137637: found: 369.137900.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06803378B2
Source dataset	uspto-grants-2004_10
ORD ID	ord-f13c6e8b7dc441729c048dc9b5886270
Source note	uspto-grants-2004_10