1,2-Dichloroethane → HCID 18403929, compound

HRID 1017682Notes

Reaction equation

HRID 1017682 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=1[O:14][CH3:15])=[O:4].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.[Cl:31]CCCl>C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH2:4].[ClH:31].[CH3:1][N:2]([CH3:16])[C:3]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][N:28]2[CH2:27][CH2:26][N:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH3:17])[CH:20]=3)[CH2:30][CH2:29]2)=[CH:8][C:7]=1[O:14][CH3:15])=[O:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 81430N-(3-methoxyphenyl)piperazineHCID 18403787HCID 18403787, compound

Product 1

HCID 18403929HCID 18403929, compound

Reagents, catalysts & solvents 1

HCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

To a solution of 4-(dimethylaminocarbonyloxy)-3-(methoxy)benzaldehyde (0.5 g) in 1,2-dichloromethane (9 ml) was added 1-(3-methoxyphenyl)piperazine (0.48 g) in 1,2-dichloroethane (1 ml) and sodium triacetoxyborohydride (0.66 g), with stirring. The reaction mixture was stirred at ambient temperature for 16 hrs, poured into ice/sodium carbonate solution and extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (silica gel), eluting with chloroform, 1% and 2% methanol:chloroform. The appropriate fractions were collected and concentrated. The residue was flash chromatographed as above. The residue was dissolved in chloroform/ether and ethereal hydrogen chloride was added. The precipitate was collected to give the analytical sample, mp 144-153° C.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 hrs
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water, saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (silica gel)
  8. washeluting with chloroform, 1% and 2% methanol
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated
  11. customchromatographed as above
  12. dissolutionThe residue was dissolved in chloroform/ether
  13. additionethereal hydrogen chloride was added
  14. customThe precipitate was collected
  15. customto give the analytical sample, mp 144-153° C.

Sources & evidence

ORD record
ord-5b26f3d0aa4d4d8db033c69ebacfa032
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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