Water → HCID 18986837, compound

HRID 2397067Notes

Reaction equation

HRID 2397067 reaction equation
[ClH:1].[CH2:2]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1)[CH2:3][CH3:4].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:1].[CH2:26]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1)[CH2:2][CH2:3][CH3:4])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 18986852HCID 18986852, compound

Product 1

HCID 18986837HCID 18986837, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

432 mg of N-n-propyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride, 0.87 ml of 1-bromo-n-hexane and 379 mg of anhydrous potassium carbonate were stirred in 4.4 ml of N,N-dimethylformamide at room temperature for 2 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered, followed by evaporation of the solvent under reduced pressure. The residue was subjected to silica gel chromatography (developing solvent; n-hexane:ethyl acetate=1:1). The target fraction was concentrated and dissolved in 2 ml of ethyl acetate. After adding 0.25 ml of a 4N solution of hydrogen chloride in ethyl acetate, the solvent was evaporated to give 358 mg of oily N-n-hexyl-N-n-propyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customfollowed by evaporation of the solvent under reduced pressure
  6. concentrationThe target fraction was concentrated
  7. dissolutiondissolved in 2 ml of ethyl acetate
  8. additionAfter adding 0.25 ml of a 4N solution of hydrogen chloride in ethyl acetate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c9dc00291dc041c59d0d4b6378f87bff
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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