Acetamide, N-(4-fluoro-3-nitrophenyl)- → HCID 57441096, compound

HRID 1987219Notes

Reaction equation

HRID 1987219 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[F:16][C:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH:18]=1>CCO>[F:16][C:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:19][CH:18]=1

Participants

4

Reactant 2

HCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-HCID 57441095HCID 57441095, compound

Product 1

HCID 57441096HCID 57441096, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Fluoro-3-nitrophenyl)acetamide (460 mg, 2.32 mmol) and [(4-fluorocyclohex-3-en-1-yl)methyl]amine hydrochloride (350 mg, 2.11 mmol) were stirred in 20 mL of EtOH containing TEA (0.735 mL, 5.28 mmol) at 75° C. for 48 h. The solvent was concentrated. The residue was dissolved in EtOAc and washed with aqueous 5% KHSO4, saturated aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by silica gel flash chromatography using 2:1/hexanes:acetone as eluent. Yield: 553 mg (85%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.51-1.61 (m, 1 H), 1.84-1.93 (m, 1 H), 1.96-2.03 (m, 2 H), 2.16-2.18 (m, 3 H), 2.22-2.32 (m, 3 H), 3.26 (m, 2 H), 5.19 (m, 1 H), 6.84 (d, J=9.37 Hz, 1 H), 7.21 (s, 1 H), 7.79 (dd, J=9.18, 2.54 Hz, 1 H), 8.09 (d, J=2.54 Hz, 2 H).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with aqueous 5% KHSO4, saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-e4b37739948d4fea800bee6c82111a0c
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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