1-(2,3-Dichlorophenyl)piperazine → HCID 21073540, compound

HRID 1373590Notes

Reaction equation

HRID 1373590 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[NH:10][C:9]2[N:8]=[C:7]([O:13][CH2:14][CH2:15][CH2:16][CH:17]=O)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:7]2[N:8]=[C:9]3[C:4]([CH:3]=[C:2]([CH3:1])[C:11](=[O:12])[NH:10]3)=[CH:5][CH:6]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8518331-(2,3-Dichlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 21073365HCID 21073365, compound

Product 1

HCID 21073540HCID 21073540, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 4-(6-methyl-7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.65 g, 2.24 mmol, 1.0 equiv) in anhydrous methanol (40 mL) cooled to 0° C. was added 2,3-dichlorophenylpiperazine (1.2 g, 4.0 mmol, 2.0 equiv). The mixture was stirred for 5 min and NaBH(OAc)3 (2.3 g, 11.2 mmol, 5.0 equiv) was added. The reaction mixture was brought to room temperature and stirred overnight. The reaction was quenched with water and was concentrated to remove methanol completely. The resultant pale green residue was dissolved in ethyl acetate and washed with 0.5 N HCl (1×10 mL), saturated NaHCO3 solution (1×10 mL) and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica gel, 2% MeOH/CH2Cl2) to afford the title compound as a white foamy solid (0.2 g, 30%). MS: ES+ 461.03, 463.03 (Exact Mass: 460.14).

Workup

  1. customwas brought to room temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched with water
  4. concentrationwas concentrated
  5. customto remove methanol completely
  6. dissolutionThe resultant pale green residue was dissolved in ethyl acetate
  7. washwashed with 0.5 N HCl (1×10 mL), saturated NaHCO3 solution (1×10 mL) and brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (silica gel, 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f0008e0ae081461baf951fca9debdc3d
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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