1,2-Dichloroethane → HCID 18403898, compound

HRID 1017689Notes

Reaction equation

HRID 1017689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH:6]=O.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O-:18])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cl:51]CCCl>>[ClH:51].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:28]2[CH2:29][CH2:30][N:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N+:16]([O-:18])=[O:17])[CH2:26][CH2:27]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13]

Participants

6

Reactant 5

HCID 111,2-Dichloroethane2×HCID 10340Sodium CarbonateHCID 1009491-(2-Nitrophenyl)piperazineHCID 4064704HCID 4064704, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18403898HCID 18403898, compoundYield 68%

Procedure

To a solution of 3-methoxy-4-(methylaminocarbonyloxy)benzaldehyde (0.60 g) in 1,2-dichloroethane (6 ml) was added 1-(2-nitrophenyl)piperazine(0.60 g) in 1,2-dichloroethane (5.5 ml), followed by sodium triacetoxyborohydride (0.92 g), with stirring. The reaction mixture was stirred for 6 hrs at ambient temperature, poured into saturated sodium carbonate solution (75 ml) and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash chromatographed (silica gel), eluting with dichloromethane, followed by 0.2, 0.5, 1.0, 2.0% methanol:dichloromethane. The appropriate fractions were collected and concentrated to give 0.78 g (68%) of product, free base. The free base was dissolved in dichloromethane, diluted with diethyl ether and ethereal hydrogen chloride was added. The precipitate was collected and recrystallized from 2-propanol to give product, mp 214-218° C.

Workup

  1. stirringThe reaction mixture was stirred for 6 hrs at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customflash chromatographed (silica gel)
  9. washeluting with dichloromethane
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e8acf33db742422d81b8c3aa1bce2bca
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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