N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochloride → HCID 66716854, compound

HRID 1184517Notes

Reaction equation

HRID 1184517 reaction equation
[CH2:1]([O:3][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)[CH3:2].Cl.Cl.[CH2:20]([NH:22][C:23](=[O:37])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[C:26]([CH3:36])[CH:25]=1)[CH3:21]>>[CH2:1]([O:3][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:33]2[CH2:32][CH2:31][N:30]([C:27]3[CH:28]=[CH:29][C:24]([C:23]([NH:22][CH2:20][CH3:21])=[O:37])=[CH:25][C:26]=3[CH3:36])[CH2:35][CH2:34]2)[CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 66926172N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochlorideHCID 718134828-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 66716854HCID 66716854, compound

Procedure

Using 398B and N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide-2HCl 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=7.07 Hz, 3H) 1.32 (t, J=6.95 Hz, 3H) 1.40 (d, J=6.57 Hz, 3H) 2.26 (s, 3H) 2.51-2.59 (m, 4H) 2.88 (br. s., 4H) 3.19-3.29 (m, 2H) 3.42 (s, 2H) 3.98-4.09 (m, 2H) 4.55-4.64 (m, 1H) 6.51 (d, J=1.52 Hz, 1H) 6.63 (d, J=1.52 Hz, 1H) 7.02 (d, J=8.34 Hz, 1H) 7.55-7.69 (m, 2H) 8.26 (t, J=5.56 Hz, 1H) 10.57 (s, 1H). ESI-MS: m/z 467.4 (M+H)+. mp 199.8-199.9° C.

Sources & evidence

ORD record
ord-b0d7a78468ea4f22adaf963120823f57
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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