Dimethylformamide → HCID 53854495, compound

HRID 1769682Notes

Reaction equation

HRID 1769682 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[O:2].[N+:9]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15](C(Br)C(N)=O)=[C:14]([Cl:24])[CH:13]=1)([O-:11])=[O:10].[C:25]([O-])([O-])=O.[K+].[K+].C[N:32]([CH:34]=[O:35])C>>[N+:9]([C:12]1[CH:13]=[C:14]([Cl:24])[C:15]([NH:32][C:34](=[O:35])[CH2:25][N:6]2[CH2:7][CH2:8][N:3]([CH:1]=[O:2])[CH2:4][CH2:5]2)=[C:16]([Cl:18])[CH:17]=1)([O-:11])=[O:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 821911-PiperazinecarboxaldehydeHCID 20096921HCID 20096921, compound

Product 1

HCID 53854495HCID 53854495, compound

Procedure

A mixture of N-formylpiperazine (0.41 mL, 4.0 mmol), (4-nitro-2,6-dichlorophenyl)-2-bromoacetamide (1.31 g, 4.0 mmol), and K2CO3 (2.2 g) in 20 mL of DMF was stirred at room temperature for 15 minutes. The mixture was then partitioned between ethyl acetate and water, the aqueous extracts were diluted with brine, and then exhaustively extracted with ethyl acetate. Solvent was removed in vacuo from the combined ethyl acetate extracts to yield the III product as a residue (1.79 g): 1H NMR (300 MHz, CDCl3) δ 2.73-2.78 (m, 2H), 2.85-2.97 (m, 4H), 3.34 (s, 2H), 3.51-3.56 (m, 1H), 3.68-3.72 (m, 1H), 8.30 (s, 2H), 9.14 (broad s, 1H).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. additionthe aqueous extracts were diluted with brine
  3. extractionexhaustively extracted with ethyl acetate
  4. customSolvent was removed in vacuo from the combined ethyl acetate
  5. customto yield the III product as a residue (1.79 g)

Sources & evidence

ORD record
ord-9d0eac06d21b4be88bae0ea767b5b7d0
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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