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

HRID 1184489Notes

Reaction equation

HRID 1184489 reaction equation
[CH2:1]([C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH:16]=O)[CH:5]=1)[CH:2]=[CH2:3].[CH2:18]([NH:20][C:21](=[O:34])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1)[CH3:19]>>[CH2:1]([C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH2:16][N:31]2[CH2:30][CH2:29][N:28]([C:25]3[CH:24]=[CH:23][C:22]([C:21]([NH:20][CH2:18][CH3:19])=[O:34])=[CH:27][CH:26]=3)[CH2:33][CH2:32]2)[CH:5]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 866642248-Allyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 667169314-(4-((8-Allyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

Procedure

Using 356A and N-ethyl-4-(piperazin-1-yl)benzamide 283 in the general procedure for reductive aminations, the title compound was obtained as an off-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) 2.43-2.49 (m, 4H) 3.18-3.29 (m, 6H) 3.30-3.32 (m, 2H) 3.39 (s, 2H) 4.61 (q, J=6.82 Hz, 1H) 5.01-5.07 (m, 2H) 5.93 (m, J=16.86, 10.17, 6.57, 6.57 Hz, 1H) 6.77 (d, J=2.02 Hz, 1H) 6.73 (d, J=2.02 Hz, 1H) 6.92 (m, 2H) 7.71 (m, 2H) 8.18 (t, J=5.56 Hz, 1H) 10.60 (br. s., 1H). ESI-MS: m/z 449.4 (M+H)+.

Sources & evidence

ORD record
ord-93d2c4b52ef74bada2461f364b8ba4cb
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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