1-(2-Pyridyl)piperazine → HCID 68876180, compound

HRID 490216Notes

Reaction equation

HRID 490216 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5](C)=[CH:4][C:3]=1[NH:9][C:10](=[O:13])[CH2:11]Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:21][CH2:22][N:23]([CH2:11][C:10]([NH:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:9][C:10](=[O:13])[CH2:11][N:23]2[CH2:22][CH2:21][N:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=3)[CH2:25][CH2:24]2)=[O:13])[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 944591-(2-Pyridyl)piperazineHCID 33838682-chloro-N-(2,5-dimethylphenyl)acetamide

Product 1

HCID 68876180HCID 68876180, compoundYield 74%

Procedure

The procedure described in Example 181 was followed, substituting 2-chloro-N-[2-(2-chloroacetylamino)phenyl]acetamide (Aldrich) for N-(2,5-dimethylphenyl)-2-chloroacetamide and using 2.4 equivalents of 1-pyridin-2-yl-piperazine to provide the title compound (74% yield) as a light tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.59 (m, 8H), 3.18 (s, 4H), 3.52 (m, 8H), 6.63 (dd, 2H, J=5.1, 5.1 Hz), 6.78 (d, 2H, J=8.5 Hz), 7.20 (dd, 2H, J=5.8, 3.4 Hz), 7.51 (dd, 2H, J=8.5, 8.5 Hz), 7.60 (dd, 2H, J=5.8, 3.7 Hz), 8.10 (d, 2H, J=3.7 Hz), 9.64 (br s, 2H); MS (DCI/NH3) m/e 515 (M+H)+; Anal. calcd for C28H34N8O2.0.4 C4H8O2.0.1 H2O: C, 64.44; H, 6.83; N, 20.31. Found: C, 64.42; H, 6.67; N, 20.12.

Sources & evidence

ORD record
ord-040f4c9214cd4bf8b7f327af18fee3df
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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