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

HRID 1184480Notes

Reaction equation

HRID 1184480 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][C:10]([CH:12]=O)=[CH:11][C:5]=2[NH:4][C:3]1=[O:20].[CH2:21]([NH:23][C:24](=[O:37])[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1)[CH3:22]>>[CH2:21]([NH:23][C:24](=[O:37])[C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:32][CH2:33][N:34]([CH2:12][C:10]3[CH:9]=[C:8]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:6]4[O:7][CH:2]([CH3:1])[C:3](=[O:20])[NH:4][C:5]=4[CH:11]=3)[CH2:35][CH2:36]2)=[CH:29][CH:30]=1)[CH3:22]

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 866642222-Methyl-3-oxo-8-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 66716918N-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

Procedure

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)+.

Sources & evidence

ORD record
ord-6f48dc2b6b3e4f47ad3e4551425662ff
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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