Sodium Carbonate → N-(2,4-Difluorophenyl)-4-(2-pyridinyl)-1-piperazineacetamide

HRID 490189Notes

Reaction equation

HRID 490189 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]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22](=[O:25])[CH2:23]Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22](=[O:25])[CH2:23][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 7358542-chloro-N-(2,4-difluorophenyl)acetamide

Product 1

HCID 3547487N-(2,4-Difluorophenyl)-4-(2-pyridinyl)-1-piperazineacetamideYield 74.8%

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-(2,4-difluorophenyl)-2-chloroacetamide (41 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 37.3 mg (74.8%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 2.52 (t, J=4 Hz, 4H), 3.23 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.08 (t, J=6 Hz, 1H), 7.38 (t, J=6 Hz, 1H), 7.92 (m, 1H), 8.12 (d, J=5 Hz, 1H), 9.60 (s, 1H); MS (ESI/APCI+) m/e 333 (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-9ff9188d66514f11a8dace1ce1cdd0ad
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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