N-ethyl-4-(piperazin-1-yl)benzamide → N-Ethyl-4-(4-((2-methyl-3-oxo-8-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	N-ethyl-4-(piperazin-1-yl)benzamide	HCID 28749590	—
Reactant	2-Methyl-3-oxo-8-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde	HCID 86664222	—
Product	N-Ethyl-4-(4-((2-methyl-3-oxo-8-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzamide	HCID 66716918	—

Reaction Steps

Using 349A and N-ethyl-4-(piperazin-1-yl)benzamide 283 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=7.20 Hz, 3H) 1.39 (d, J=6.82 Hz, 3H) 2.51-2.55 (m, 4H) 3.19-3.30 (m, 6H) 3.48 (s, 2H) 4.67 (q, J=6.57 Hz, 1H) 6.87-6.97 (m, 4H) 7.31-7.38 (m, 1H) 7.40-7.47 (m, 2H) 7.51-7.56 (m, 2H) 7.71 (d, J=8.84 Hz, 2H) 8.17 (t, J=5.68 Hz, 1H) 10.72 (br. s., 1H). ESI-MS: m/z 485.4 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669249B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-6f48dc2b6b3e4f47ad3e4551425662ff
Source note	uspto-grants-2014_03