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

HRID 1184485Notes

Reaction equation

HRID 1184485 reaction equation
[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH:20]=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][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>>[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH2:20][N:34]2[CH2:35][CH2:36][N:31]([C:28]3[CH:27]=[CH:26][C:25]([C:24]([NH:23][CH3:22])=[O:37])=[CH:30][CH:29]=3)[CH2:32][CH2:33]2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 28749530N-methyl-4-(piperazin-1-yl)benzamideHCID 86664223HCID 86664223, compound

Product 1

HCID 667170914-(4-((8-Benzyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-methylbenzamide

Procedure

Using 353A and N-methyl-4-(piperazin-1-yl)benzamide 282 in the general procedure for reductive aminations, the title compound was obtained as a light grey solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (d, J=6.82 Hz, 3H) 2.42-2.49 (m, 4H) 2.74 (d, J=4.29 Hz, 3H) 3.16-3.28 (m, 4H) 3.38 (s, 2 H) 3.89 (s, 2H) 4.54-4.60 (m, 1H) 6.73-6.82 (m, 2H) 6.92 (m, 2H) 7.14-7.19 (m, 1H) 7.19-7.23 (m, 2H) 7.24-7.30 (m, 2H) 7.70 (m, 2H) 8.14 (q, J=4.29 Hz, 1H) 10.60 (s, 1H). ESI-MS: m/z 485.4 (M+H)+. mp=227.0-230.9° C.

Sources & evidence

ORD record
ord-71113dba0cbd4e0ea7988369e37b59dc
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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