Sodium Carbonate → HCID 21278906, compound

HRID 2291564Notes

Reaction equation

HRID 2291564 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].F[C:11]1[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH3:17])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH3:17])[CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 837951-AcetylpiperazineHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 21278906HCID 21278906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Acetylpiperazine (6.23 g), 5-fluoro-2-nitrotoluene (7.51 g) and sodium carbonate (5.12 g) in dimethylformamide (40 ml) were stirred at 100° overnight, evaporated, and the residue partitioned between ethyl acetate and water. The organic layer was dried (sodium sulphate), evaporated, and the residue chromatographed over Merck (Trade Mark) t.l.c. grade silica, developing and eluting with 5% methanol in dichloromethane, yield 10.92 g of the title compound. A small portion was recrystallized from methanol/ethyl acetate, m.p. 133°-7°.

Workup

  1. customevaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulphate)
  4. customevaporated
  5. customthe residue chromatographed over Merck (Trade Mark)
  6. washeluting with 5% methanol in dichloromethane, yield 10.92 g of the title compound
  7. customA small portion was recrystallized from methanol/ethyl acetate, m.p. 133°-7°

Sources & evidence

ORD record
ord-fac6d1f1007a492d97e48178d728ad2b
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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