Dipropylamine → HCID 10596406, compound

HRID 2397065Notes

Reaction equation

HRID 2397065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH2:17][CH2:18][CH2:19][CH2:20]Cl)[CH:3]=1.[CH2:22]([NH:25][CH2:26][CH2:27][CH3:28])[CH2:23][CH3:24]>C(Cl)Cl>[CH2:22]([N:25]([CH2:20][CH2:19][CH2:18][CH2:17][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:26][CH2:27][CH3:28])[CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 18986900HCID 18986900, compound

Product 1

HCID 10596406HCID 10596406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

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. washthe mixture was successively washed with a saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  3. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-78ecf544e99244c89dead1f8e2139cd3
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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