Sodium Carbonate → N-(2-methylphenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide

HRID 490190Notes

Reaction equation

HRID 490190 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:24])[CH2:22]Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:24])[CH2:22][N:10]1[CH2:9][CH2:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 101479Acetamide, 2-chloro-N-(2-methylphenyl)-

Product 1

HCID 10358049N-(2-methylphenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(2-methyl-phenyl)-2-chloroacetamide (37 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 29.3 mg (63%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 2.23 (s, 3H), 2.62 (t, J=4 Hz, 4H), 3.20 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.05 (t, J=6 Hz, 1H), 7.10 (m, 2H), 7.58 (t, J=5 Hz, 1H), 7.78 (d, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 9.40 (s, 1H); MS (ESI/APCI+) m/e 311 (M+H)+.

Workup

  1. customThe resulting mixture was decanted
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-d3fd871c2e7444a0ba4976baded35a99
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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