Sodium Carbonate → N-(4-fluorophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamide

HRID 490188Notes

Reaction equation

HRID 490188 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:24])[CH2:22]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[F:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:24])[CH2:22][N:10]2[CH2:9][CH2:8][N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 5320652-chloro-N-(4-fluorophenyl)acetamide

Product 1

HCID 3592987N-(4-fluorophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamideYield 95.4%

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-(4-fluorophenyl)-2-chloroacetamide (38 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 45 mg (95%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 2.60 (m, 4H), 3.18 (s, 2H), 3.58 (m, 4H), 6.63 (m, 1H), 6.83 (d, J=5 Hz, 1H), 7.14 (dd, J=8.7, 8.7 Hz, 2H), 7.55 (m, 1H), 7.66 (m, 2H), 8.18 (d, J=5 Hz, 1H), 9.80 (s, 1H); MS (ESI/APCI+) m/e 315 (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-7176752a096a4f30b00285b48335b4ea
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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