3-Chloro-N-ethyl-4-(piperazin-1-yl)benzamide → HCID 66717105, compound

HRID 1184522Notes

Reaction equation

HRID 1184522 reaction equation
[F:1][CH:2]([F:18])[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.[Cl:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:23]([NH:25][CH2:26][CH3:27])=[O:24]>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=1[N:31]1[CH2:32][CH2:33][N:34]([CH2:16][C:6]2[CH:5]=[C:4]([O:3][CH:2]([F:18])[F:1])[C:9]3[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=3[CH:7]=2)[CH2:35][CH2:36]1)[C:23]([NH:25][CH2:26][CH3:27])=[O:24]

Participants

3

Reactant 2

HCID 583244573-Chloro-N-ethyl-4-(piperazin-1-yl)benzamideHCID 86664227HCID 86664227, compound

Product 1

HCID 66717105HCID 66717105, compound

Procedure

Using 403A and 3-chloro-N-ethyl-4-(piperazin-1-yl)benzamide 286 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3H) 1.39-1.46 (m, 3H) 2.52-2.61 (m, 4H) 3.05 (br. s., 4H) 3.21-3.30 (m, 2H) 3.45 (s, 2H) 4.70-4.78 (m, 1H) 6.78-6.83 (m, 2H) 7.13-7.21 (m, 2H) 7.77 (dd, J=8.59, 2.02 Hz, 1H) 7.87 (d, J=2.02 Hz, 1H) 8.43 (t, J=5.56 Hz, 1H) 10.81 (s, 1H). ESI-MS: m/z 509.3 (M+H)+. mp 101.7-104.0° C.

Sources & evidence

ORD record
ord-eeac5295aab44beea2e697f7528f9ee0
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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