Oxalic Acid → HCID 18986873, compound

HRID 2397066Notes

Reaction equation

HRID 2397066 reaction equation
[CH2:1]([N:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>C(O)C>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[CH2:1]([N:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 10596406HCID 10596406, compound

Product 1

HCID 18986873HCID 18986873, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 0.91 g of the crude 4-chloro-2-(4-chlorobutyl)-1-(2-phenylethoxy)benzene, was added 10 ml of di-n-propylamine and the resulting mixture was stirred at 120° C. for 38 hours. After diluting with methylene chloride, the mixture was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:6) to give 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine. To a solution of 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine in 10 ml of ethanol, was added a solution of 123 mg of oxalic acid in 5 ml of ethanol. After evaporation of the solvent under reduced pressure, the obtained crystals were recrystallized from ethyl acetate to give 421 mg of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine oxalate.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1125d6cf68d741dfbf98a641fa20551d
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

Loading…